Imidazopyrimidine and imidazotriazine derivative, and pharmaceutical composition comprising the same

ABSTRACT

The present disclosure provides a compound of Chemical Formula (1) or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same: 
     
       
         
         
             
             
         
       
         
         
           
             wherein X, Z, R 1  and R 2  are as defined in the specification. 
           
         
       
    
     The compound of Chemical Formula (1) or pharmaceutically acceptable salt thereof acts as a positive allosteric modulator of metabotropic glutamate receptor subtype 5 (mGluR5), thereby being useful in the prevention or treatment of disorder mediated by glutamate dysfunction and mGluR5.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a non-provisional application claiming priority toKorean Patent Application No. 10-2015-0027395, filed on 26 Feb. 2015.The entire disclosure of the application identified in this paragraph isincorporated herein by reference.

FIELD

The present disclosure generally relates to a compound modulatingreceptor activity, pharmaceutical compositions comprising the compound,and methods useful for treating diseases. The present disclosure relatesto a compound useful as a positive allosteric modulator (PAM) ofmetabotropic glutamate receptor subtype 5 (mGluR5) or a pharmaceuticallyacceptable salt thereof, and a pharmaceutical composition for theprevention and/or treatment of disorders mediated by glutamatedysfunction and mGluR5 comprising a therapeutically effective amount ofthe same.

BACKGROUND

Glutamate is the most prevalent excitatory neurotransmitter in thecentral nervous system (CNS) of mammals. Glutamate plays an importantrole in numerous physiological functions such as cardiovascularregulation, perception and recognition, and synaptogenesis as well aslearning and memory. As such, in the occurrence of imbalance inglutamate neurotransmission, various nervous and mental diseases such asschizophrenia may be caused, and thus glutamate plays an important rolein physiology.

Glutamate mediates synaptic neurotransmission via ionotropic glutamatereceptors (iGluR)—i.e., the activation of NMDA receptors, AMPA receptorsand kainate receptors involved in rapid excitatory transmission(Nakanishi S. et al., Brain Res. Rev., (1998) 26: 230-235). In addition,glutamate plays a role in subtly regulating excitatory synapticneurotransmission via the activation of metabotropic glutamate receptor(mGluR).

Metabotropic glutamate receptors (mGluR) consist of eight (8) subtypesand are sub-divided into three groups (Groups I, II and III) accordingto arrangement, homology and pharmacological property. mGluR5 belongs toGroup I, and it is known that mGluR5 interacts with NMDA receptors viavarious proteins and neurotransmission pathways. Therefore, because thebalance of deficiency or hyperactivity of physiological function by NMDAreceptors can be regulated via the modulation of mGluR5, to modulatemGluR5 is very important.

Since a variety of pathophysiological processes and disease statesaffecting the CNS are thought to be related to abnormal glutamateneurotransmission and NMDA receptor malfunction, modulators of mGluR5receptors could be therapeutically beneficial in the treatment ofvarious CNS diseases. Moreover, because mGluR5 receptor modulators whichact through allosteric binding site have some advantages such as subtypeselectivity, brain penetration and safety potential, many studies havereported that the mGluR5 positive allosteric modulators were useful forthe treatment of schizophrenia and CNS diseases.

International Publication Nos. WO 2008/151184 and WO 2011/035324disclose benzamide and O-benzyl nicotinamide derivatives as an mGluR5positive allosteric modulator, respectively. International PublicationNo. WO 2010/124055 discloses 2-alkyl piperidine derivatives as an mGluR5positive allosteric modulator, and International Publication No. WO2011/082010 discloses tetrahydrotriazolopyridine derivative compounds.International Publication Nos. WO 2012/078817 and WO 2012/083224disclose bicyclic pyrazole and bicyclic triazole compounds as an mGluR5positive allosteric modulator, respectively.

SUMMARY

In an embodiment, there is provided imidazopyrimidine andimidazotriazine derivative compound as a positive allosteric modulatorof metabotropic glutamate receptor subtype 5 (mGluR5) or apharmaceutically acceptable salt thereof.

In another embodiment, there is provided a pharmaceutical compositioncomprising the above imidazopyrimidine and imidazotriazine derivativecompound or a pharmaceutically acceptable salt thereof as an activeingredient.

The present inventors have synthesized imidazopyrimidine andimidazotriazine derivative compounds of Chemical Formula (1) andconfirmed that said compounds show effective and selective effects as apositive allosteric modulator of metabotropic glutamate receptor subtype5 (mGluR5), thereby being useful in the treatment of disorders mediatedby glutamate dysfunction and mGluR5 such as schizophrenia.

DETAILED DESCRIPTION

The following description is merely exemplary in nature and is notintended to limit the present disclosure, application, or uses.

The present disclosure provides a compound of Chemical Formula (1) and apharmaceutically acceptable salt thereof:

wherein

X represents CH or N;

Z represents O or S;

R₁ represents aryl which is unsubstituted or substituted with one ormore substituents selected from halo, hydroxy, alkyl, alkoxy, alkylthio,amino, dialkylamino, cyano, formyl, haloalkyl, hydroxyalkyl,alkoxyalkyl, carbamoyloxy alkyl, alkyl-C(O)O-alkyl, dialkylaminoalkyland 5- or 6-membered heterocycloalkylalkyl in which the heterocycloalkylhas 1-3 heteroatoms selected from N, O and S; or 5- to 12-membered,unsaturated heterocyclyl having 1-5 heteroatoms selected from N, O andS, which is unsubstituted or substituted with one or more substituentsselected from halo, hydroxy, alkyl, alkoxy and haloalkyl; and

R₂ represents aryl which is unsubstituted or substituted with one ormore substituents selected from halo, deuterium, hydroxy and alkyl; or5- to 12-membered, unsaturated heterocyclyl having 1-3 heteroatomsselected from N, O and S, which is unsubstituted or substituted with oneor more substituents selected from halo and alkyl.

In a particular embodiment, R₁ represents aryl which is unsubstituted orsubstituted with one or more substituents selected from halo, hydroxy,C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino,cyano, formyl, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅alkyl, carbamoyloxy-C₁-C₅ alkyl, C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl, di(C₁-C₅alkyl)amino-C₁-C₅ alkyl and 5- or 6-membered heterocycloalkyl-C₁-C₅alkyl wherein the heterocycloalkyl has 1-3 heteroatoms selected from N,O and S; or 5- to 12-membered, unsaturated heterocyclyl having 1-5heteroatoms selected from N, O and S, which is unsubstituted orsubstituted with one or more substituents selected from halo, hydroxy,C₁-C₅ alkyl, C₁-C₅ alkoxy and halo-C₁-C₅ alkyl; and R₂ represents arylwhich is unsubstituted or substituted with one or more substituentsselected from halo, deuterium, hydroxy and C₁-C₅ alkyl; or 5- to12-membered, unsaturated heterocyclyl having 1-3 heteroatoms selectedfrom N, O and S, which is unsubstituted or substituted with one or moresubstituents selected from halo and C₁-C₅ alkyl.

Unless stated otherwise, herein the term “alkyl,” either alone or incombination with further terms (for example, haloalkyl), means a radicalof saturated aliphatic hydrocarbyl group having 1 to 5 carbon atoms,which may be linear or branched. Examples of representative alkyl groupinclude, but are not limited to, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl,neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl and1,2-dimethylpropyl.

Unless stated otherwise, herein the term “halo,” either alone or incombination with further terms (for example, haloalkyl), means a radicalof F, Cl, Br or I.

Unless stated otherwise, herein the term “heterocycloalkyl” means a 5-or 6-membered, saturated monocyclic ring having 1 to 3 heteroatomsselected from N, O and S, and preferably a 5- or 6-membered, saturatedmonocyclic ring having 1 or 2 heteroatoms selected from N and O.Concrete examples of heterocycloalkyl include, but are not limited to,pyrrolidinyl, piperidinyl, tetrahydrofuranyl, tetrahydropyranyl andmorpholinyl.

Unless stated otherwise, herein the term “aryl” means an aromaticradical having 6 to 12 carbon atoms. Concrete examples of aryl include,but are not limited to, phenyl and naphthyl.

Unless stated otherwise, herein the term “unsaturated heterocyclyl”means a 5- or 12-membered, unsaturated monocyclic or bicyclic ringhaving 1 to 5 heteroatoms selected from N, O and S. Concrete examples ofunsaturated heterocyclyl include, but are not limited to,1,3-benzodioxolyl, or heteroaryl such as pyridyl, pyrimidinyl, thienyl,pyrazinyl, quinolinyl and isoquinolinyl.

According to one aspect of the present disclosure, R₁ is selected fromthe group consisting of:

wherein n is 0, 1, 2, 3 or 4; each R₃ is selected from halo, hydroxy,C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino,cyano, formyl, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅alkyl, carbamoyloxy-C₁-C₅ alkyl, C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl, di(C₁-C₅alkyl)amino-C₁-C₅ alkyl and 5- or 6-membered heterocycloalkyl-C₁-C₅alkyl; and each R₄ is selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅alkoxy and halo-C₁-C₅ alkyl; and

R₂ is selected from the group consisting of:

wherein m is 0, 1, 2, 3 or 4; R₅ is selected from halo, deuterium,hydroxy and C₁-C₅ alkyl; and R₅ is selected from halo and C₁-C₅ alkyl.

According to one aspect of the present disclosure, in Chemical Formula(1), R₁ represents phenyl which is unsubstituted or substituted with 1to 3 substituents selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino, cyano, formyl,halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅ alkyl,carbamoyloxy-C₁-C₅ alkyl and C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl; or 5- to10-membered, unsaturated heterocyclyl having 1-3 heteroatoms selectedfrom N, O and S, which is unsubstituted or substituted with 1 to 3substituents selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy andhalo-C₁-C₅ alkyl.

According to another aspect of the present disclosure, in ChemicalFormula (1), R₂ represents phenyl unsubstituted or substituted with 1 to5 substituents selected from halo, deuterium, hydroxy and C₁-C₅ alkyl;or 5- or 6-membered heteroaryl having 1 to 3 heteroatoms selected fromN, O and S, which is unsubstituted or substituted with 1 to 3substituents selected from halo and C₁-C₅ alkyl.

According to still another aspect of the present disclosure, in ChemicalFormula (1),

X represents CH or N;

Z represents O;

R₁ represents phenyl which is unsubstituted or substituted with 1 to 3substituents selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy,C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino, cyano, formyl, halo-C₁-C₅alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅ alkyl, carbamoyloxy-C₁-C₅alkyl and C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl; or 5- to 9-membered,unsaturated heterocyclyl having 1 or 2 heteroatoms selected from N, Oand S, which is unsubstituted or substituted with 1 or 2 substituentsselected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy and halo-C₁-C₅alkyl; and

R₂ represents phenyl which is unsubstituted or substituted with 1 to 5substituents selected from halo, deuterium, hydroxy and C₁-C₅ alkyl; or6-membered heteroaryl having 1 or 2 nitrogen atoms, which isunsubstituted or substituted with 1 or 2 substituents selected from haloand C₁-C₅ alkyl.

According to still another aspect of the present disclosure, in ChemicalFormula (1),

R₁ represents phenyl which is unsubstituted or substituted with 1 to 3substituents selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy,C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino, cyano, formyl, halo-C₁-C₅alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅ alkyl, carbamoyloxy-C₁-C₅alkyl and C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl; 1,3-benzodioxolyl which isunsubstituted or substituted with 1 or 2 halo; or pyridyl or pyrimidinylwhich is unsubstituted or substituted with 1 or 2 substituents selectedfrom halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy and halo-C₁-C₅ alkyl; and

R₂ represents phenyl which is unsubstituted or substituted with 1 to 5substituents selected from halo, deuterium, hydroxy and C₁-C₅ alkyl; orpyridyl which is unsubstituted or substituted with 1 or 2 substituentsselected from halo and C₁-C₅ alkyl.

According to still another aspect of the present disclosure, in ChemicalFormula (1),

X represents CH;

Z represents O;

R₁ represents phenyl which is unsubstituted or substituted with 1 to 3substituents selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy,C₁-C₅ alkylthio, amino, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl and C₁-C₅alkoxy-C₁-C₅ alkyl; and

R₂ represents pyridyl which is unsubstituted or substituted with 1 or 2substituents selected from halo and C₁-C₅ alkyl.

In an embodiment, there is provided a compound of Chemical Formula (2)or a pharmaceutically acceptable salt thereof:

wherein n is 0, 1, 2 or 3;

each R₃ is independently selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino, cyano, formyl,halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅ alkyl,carbamoyloxy-C₁-C₅ alkyl, C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl, di(C₁-C₅alkyl)amino-C₁-C₅ alkyl and 5- or 6-membered heterocycloalkyl-C₁-C₅alkyl wherein the heterocycloalkyl has 1-3 heteroatoms selected from N,O and S;

m is 0, 1, 2 or 3; and

each R₆ is independently selected from halo and C₁-C₅ alkyl.

In various embodiments, n is 0, 1 or 2; each R₃ is selected from halo,halo-C₁-C₅ alkyl, C₁-C₅ alkyl, and hydroxy-C₁-C₅ alkyl; m is 0 or 1; andR₆ is halo. In a particular embodiment, n is 1 or 2; each R₃ is selectedfrom fluoro, fluoromethyl, trifluoromethyl, methyl, and hydroxymethyl; mis 0 or 1; and R₆ is fluoro.

The compounds of Chemical Formula (1) according to the presentdisclosure include, but are not limited to, the following compounds:

-   6-(2-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   2-phenoxymethyl-6-phenylimidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2,3-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-amino-6-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-dimethylaminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-trifluoromethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-methoxy-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-3-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-chloro-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-cyano-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(7-fluorobenzo[1,3]dioxol-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxymethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylthiophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2,4-difluoro-5-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-methoxypyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-methylpyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2,6-difluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-chloropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-fluoropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-chloropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-chlorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-fluoro-4-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-fluoro-5-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(5-fluoro-2-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-3-hydroxyphenyl)-2-(3-fluorophenoxymethyl)-imidazo[1,2-a]pyrimidine;-   6-(2-aminophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-chloropyridin-4-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-methylpyridin-3-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-chloropyridin-4-yl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,6-dimethylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;-   4-[[6-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-2-yl]methoxy]phenol;-   2-[(4-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;-   2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;-   2-[(4-fluorophenoxy)methyl]-6-phenyl-imidazo[1,2-a]pyrimidine;-   5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;-   5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;-   6-(4-fluorophenyl)-2-[(2,3,4,5,6-pentadeuteriophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]6-(o-tolyl)imidazo[1,2-a]pyrimidine;-   6-(5-fluoro-2-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;-   6-(2-fluoro-4-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;-   2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   6-(2-chloro-4-fluoro-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   4-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;-   6-(4-chloro-2-methoxy-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   6-(2,6-difluoro-3-pyridyl)-2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methyl-aniline;-   4,5-difluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-5-methyl-aniline;-   5-chloro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;-   5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   2-[(4-fluorophenoxy)methyl]-6-(4-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;-   6-(5,6-difluoro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methoxy-aniline;-   2-[(4-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-2-pyridyl)imidazo[1,2-a]pyrimidine;-   6-(4-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   6-(5-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-3-pyridyl)imidazo[1,2-a]pyrimidine;-   5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-ol;-   6-(6-fluoro-5-methyl-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(6-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   4-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;-   [5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   [5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   6-(4-fluoro-2-methylsulfanyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(2-methoxy-4-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;-   5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   6-(4-fluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,3-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(5-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(7-fluoro-2H-benzo[1,3]dioxol-4-yl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-chloro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-fluoro-2-methoxy-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-[4-fluoro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-ethylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methyl-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-fluoro-4-methyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,3-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   2-[(4-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   2-[(5-fluoro-2-pyridyl)oxymethyl]-6-(o-tolyl)imidazo[1,2-a]pyrimidine;-   6-(4-chloro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-dimethylphenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   2-(2-pyridyloxymethyl)-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;-   2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;-   6-(5-fluoro-2-pyridyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   2-fluoro-5-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   2-fluoro-5-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]aniline;-   [5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   3-methoxy-4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;-   4-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;-   6-(4-fluoro-2-methylsulfanyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   [5-fluoro-2-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;-   6-[4-fluoro-2-(methoxymethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   [2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-5-(trifluoromethyl)phenyl]methanol;-   6-(2-isopropylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-3-(trifluoromethyl)benzaldehyde;-   6-[4-chloro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(5-chloropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,3-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxymethylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-[(5-fluoro-3-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   2-[(2-chloro-4-pyridyl)oxymethyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;-   2-[(5-fluoro-3-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   2-[(2-fluoro-4-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   5-fluoro-2-[2-[(2-fluoro-4-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   [5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   2-(2,4-difluorophenyl)-6-(phenoxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2,4-difluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2,4-difluorophenyl)-6-((pyridin-2-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2-methylphenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2,4-difluorophenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluoro-2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-[4-fluoro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(3-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-[4-chloro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-chloro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluoro-2-methyl-phenyl)-6-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine;-   [5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methyl    carbamate;-   [5-fluoro-2-[2-(phenoxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methyl    carbamate;-   [5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methyl    carbamate;-   [5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methyl    acetate;-   6-[2-(chloromethyl)-4-fluoro-phenyl]-2-[(4-fluorophenoxy)methyl)imidazo[1,2-a]pyrimidine;-   6-[4-fluoro-2-(fluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;    and-   6-[4-fluoro-2-(fluoromethyl)phenyl]-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine.

In various embodiments, R₁ and R₂ are optionally substituted phenyl andsuch compounds include, but are not limited to, the following compounds:

-   6-(2-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   phenoxymethyl-6-phenylimidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2,3-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-amino-6-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-dimethylaminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-trifluoromethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-methoxy-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-3-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-chloro-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-cyano-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(7-fluorobenzo[1,3]dioxol-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxymethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylthiophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2,4-difluoro-5-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-chlorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-3-hydroxyphenyl)-2-(3-fluorophenoxymethyl)-imidazo[1,2-a]pyrimidine;-   6-(2-aminophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,6-dimethylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   4-[[6-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-2-yl]methoxy]phenol;-   2-[(4-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;-   2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;-   2-[(4-fluorophenoxy)methyl]-6-phenyl-imidazo[1,2-a]pyrimidine;-   5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;-   5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;-   6-(4-fluorophenyl)-2-[(2,3,4,5,6-pentadeuteriophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]6-(o-tolyl)imidazo[1,2-a]pyrimidine;-   6-(5-fluoro-2-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;-   6-(2-fluoro-4-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   6-(2-chloro-4-fluoro-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   4-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;-   6-(4-chloro-2-methoxy-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methyl-aniline;-   4,5-difluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-5-methyl-aniline;-   5-chloro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;-   5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methoxy-aniline;-   2-[(3-fluorophenoxy)methyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   4-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;-   [5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   [5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   6-(4-fluoro-2-methylsulfanyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;-   5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   2-(2,4-difluorophenyl)-6-(phenoxymethyl)imidazo[1,2-b][1,2,4]triazine;-   [5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methyl    carbamate;-   [5-fluoro-2-[2-(phenoxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methyl    carbamate-   6-[2-(chloromethyl)-4-fluoro-phenyl]-2-[(4-fluorophenoxy)methyl)imidazo[1,2-a]pyrimidine;    and-   6-[4-fluoro-2-(fluoromethyl)phenyl]-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine.

In various embodiments, R₁ is optionally substituted pyridinyl and R₂ isoptionally substituted phenyl, and such compounds include, but are notlimited to, the following compounds:

-   6-(2-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-methoxypyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(4-methylpyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2,6-difluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-chloropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(2-fluoropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-chloropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-fluoro-4-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(6-fluoro-5-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(5-fluoro-2-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;-   6-(3-chloropyridin-4-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-methylpyridin-3-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-chloropyridin-4-yl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;-   6-(2,6-difluoro-3-pyridyl)-2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(4-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;-   6-(5,6-difluoro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-2-pyridyl)imidazo[1,2-a]pyrimidine;-   6-(4-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   6-(5-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-3-pyridyl)imidazo[1,2-a]pyrimidine;-   5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-ol;-   6-(6-fluoro-5-methyl-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;-   2-[(4-fluorophenoxy)methyl]-6-(6-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;-   2-[(3-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;    and-   2-[(4-fluorophenoxy)methyl]-6-(2-methoxy-4-pyridyl)imidazo[1,2-a]pyrimidine.

In various embodiments, R₁ is optionally substituted phenyl and R₂ isoptionally substituted pyridinyl, and such compounds include, but arenot limited to, the following compounds:

-   6-(4-fluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,3-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(5-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(7-fluoro-2H-benzo[1,3]dioxol-4-yl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-chloro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-fluoro-2-methoxy-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-[4-fluoro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-ethylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methyl-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-fluoro-4-methyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,3-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(3-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   2-[(4-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   2-[(5-fluoro-2-pyridyl)oxymethyl]-6-(o-tolyl)imidazo[1,2-a]pyrimidine;-   6-(4-chloro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-dimethylphenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   2-fluoro-5-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   2-fluoro-5-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]aniline;-   [5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   3-methoxy-4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;-   4-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;-   6-(4-fluoro-2-methylsulfanyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   [5-fluoro-2-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;-   6-[4-fluoro-2-(methoxymethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   [2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-5-(trifluoromethyl)phenyl]methanol;-   6-(2-isopropylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-3-(trifluoromethyl)benzaldehyde;-   6-[4-chloro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(5-chloropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,4-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-methoxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2,3-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluoro-2-hydroxymethylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;-   6-(4-fluorophenyl)-2-[(5-fluoro-3-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;-   2-[(2-chloro-4-pyridyl)oxymethyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;-   2-[(5-fluoro-3-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   2-[(2-fluoro-4-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;-   5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   5-fluoro-2-[2-[(2-fluoro-4-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;-   [5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;-   2-(2,4-difluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2,4-difluorophenyl)-6-((pyridin-2-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2-methylphenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2,4-difluorophenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluoro-2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-(2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;-   2-[4-fluoro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(3-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-[4-chloro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-chloro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;-   2-(4-fluoro-2-methyl-phenyl)-6-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine;-   [5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methyl    carbamate;-   [5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methyl    acetate; and-   6-[4-fluoro-2-(fluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine.

In various embodiments, both R₁ and R₂ are optionally substitutedpyridinyl, and such compounds include, but are not limited to, thefollowing compounds:

-   2-(2-pyridyloxymethyl)-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;-   2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;    and-   6-(5-fluoro-2-pyridyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine.

As described herein, it is confirmed that the compounds of ChemicalFormula (1) are effective as a positive allosteric modulator ofmetabotropic glutamate receptor subtype 5 (mGluR5 PAM). Also, they haveselective activity as a positive allosteric modulator of mGluR5 PAM.Such medicinal effects of the compounds of Chemical Formula (1) can bemaintained in the form of pharmaceutically acceptable salts.

Therefore, in still another aspect of the present disclosure, there isprovided a pharmaceutical composition for the prevention or treatment ofdisorder mediated by glutamate dysfunction and metabotropic glutamatereceptor subtype 5 (mGluR5) comprising a therapeutically effectiveamount of the compound of Chemical Formula (1) or a pharmaceuticallyacceptable salt thereof as an active ingredient, together with apharmaceutically acceptable carrier or excipient. The pharmaceuticalcomposition may further comprise one or more additives selected from thegroup consisting of a pharmaceutically acceptable carrier, diluent andadjuvant.

Specifically, the pharmaceutical composition may be a composition for apositive allosteric modulator of mGluR5.

In addition, the pharmaceutical composition may be a composition for theprevention and/or treatment of disorders mediated by glutamatedysfunction and mGluR5. The disorders mediated by glutamate dysfunctionand mGluR5 may be, for example, schizophrenia, and include any disordersknown as being related to glutamate dysfunction and mGluR5. In thisregard, the article (N. Matosin et al., Schizophrenia Research, 2013,Vol. 146, pp. 170-176) reported the relation between a positiveallosteric modulator of mGluR5 and the treatment of schizophrenia.

The pharmaceutically acceptable salt includes any acid or base additionsalts, and any stereochemical isomer thereof. These salts are notspecifically limited and may be any salt that is able to retain activityof a parent compound thereof in a target subject and does not cause anyundesirable effect. Examples of these salts are both inorganic andorganic salts, such as acetic acid, nitric acid, aspartic acid, sulfonicacid, sulfuric acid, maleic acid, glutamic acid, formic acid, succinicacid, phosphoric acid, phthalic acid, tannic acid, tartaric acid,hydrobromic acid, propionic acid, benzenesulfonic acid, benzoic acid,stearic acid, cresylic acid, lactic acid, bicarbonic acid, bisulfuricacid, bitartaric acid, oxalic acid, butylic acid, calcium edatate,camsylic acid, carbonic acid, chlorobenzoic acid, citric acid, edeticacid, toluenesulfonic acid, edicylinic acid, ecylinic acid, fumaricacid, gluceptic acid, pamoic acid, gluconic acid, glycollarsanylic acid,methyl nitrate, polygalactronic acid, hexyllisorcynonic acid, malonicacid, hydrobamic acid, hydrochlorinic acid, hydroiodic acid,hydroxynaphtholic acid, isethionic acid, lactobionic acid, mandelicacid, estolinic acid, mucic acid, muconic acid, p-nitromethanesulfonicacid, hexamic acid, phantothenic acid, monohydrogen phosphoric acid,dihydrogen phosphoric acid, salicylic acid, sulfamine acid, sulfanilicacid, methanesulfonic acid and theoclic acid. In addition, examples of abasic salt are an ammonium salt, a salt of an alkali or alkali earthmetal such as lithium, sodium, potassium, magnesium, or calcium, a saltcontaining an organic base such as benzathine, N-methyl-D-glucamine, orhydrabamine, and a salt containing an amino acid such as arginine orlysine. These salts may be converted into a free form by treatment withappropriate acid or base. The term “addition salt” may be taken toinclude solvates obtainable from any of the compounds of ChemicalFormula (1) and salts thereof. Examples of these solvates are hydratesand alcoholates.

The pharmaceutical composition may be formulated into various types fororal or parenteral administration. For example, it may be formulatedinto any dosage form for oral administration such as tablets, pills,soft/hard capsules, solutions, suspensions, emulsions, syrups, granulesand elixirs. Besides the effective ingredient, such a dosage form fororal administration may further include any pharmaceutically acceptablecarriers depending on a typical construction of each formulation—forexample, diluents such as lactose, dextrose, sucrose, mannitol,sorbitol, cellulose and/or glycine, or lubricants such as silica, talc,steric acid and its magnesium or calcium salt, and/or polyethyleneglycol.

In addition, in case the formulation for oral administration is in atablet form, it may also comprise binding agents such magnesium aluminumsilicate, starch paste, gelatin, gum tragacanth, methyl cellulose,sodium carboxymethyl cellulose, and/or polyvinyl pyrrolidone, and ifdesired, it may also include disintegrating agents such as starch, agar,or alginic acid or its sodium salt, or a boiling mixture, and/or anabsorbing agent, a colorant, a flavoring agent, or a sweetening agent.

The pharmaceutical composition may be formulated into a form ofparenteral administration. In this case, it may be administered by meansof parenteral administration methods such as a hypodermic injection, anintravenous injection, an intramuscular injection or an intrathoracicinjection. In order for the pharmaceutical composition of the presentdisclosure to be formulated into a dosage form for parenteraladministration, the effective ingredient (i.e., the compound of ChemicalFormula (1) or a pharmaceutically acceptable salt thereof) may be mixedwith a stabilizer or a buffering agent in water to prepare as a solutionor a suspension, and this solution or suspension may then be produced asa unit dosage form such as an ampoule or a vial.

In addition, the pharmaceutical composition may be sterilized or mayfurther comprise an adjuvant such as a preservative, a stabilizingagent, a hydrating agent, an emulsifying agent, or a salt forcontrolling osmotic pressure and/or a buffering agent, and it mayfurther include other therapeutically beneficial substances and may beformulated in accordance with conventional methods of mixing,granulation or coating.

The pharmaceutical composition may comprise the effectiveingredient—i.e., the compound of Chemical Formula (1) or apharmaceutically acceptable salt thereof in an effective amount of 0.1to 500 mg/kg (body weight), preferably 0.5 to 100 mg/kg (body weight)per day in case of mammals including a human, and such a pharmaceuticalcomposition may be divided into one, or two or more doses per day andadministered via an oral or parenteral route.

In still another aspect, the present disclosure also provides a role asa positive allosteric modulator of metabotropic glutamate receptorsubtype 5 (mGluR5), comprising the step of administering atherapeutically effective amount of the compound of Chemical Formula (1)or a pharmaceutically acceptable salt thereof to a patient in needthereof. The modulation method may further comprise a step ofidentifying the patient who is in need of positive allosteric modulationof mGluR5 prior to the step of administration.

In addition, the present disclosure provides a method for the preventionand/or treatment of disorders mediated by glutamate dysfunction andmGluR5, comprising the step of administering a therapeutically effectiveamount of the compound of Chemical Formula (1) or a pharmaceuticallyacceptable salt thereof to a patient in need thereof. The method for theprevention and/or treatment may further comprise a step of identifyingthe patient who is in need of the prevention and/or treatment ofdisorders mediated by glutamate dysfunction and mGluR5 prior to the stepof administration.

The disorders mediated by glutamate dysfunction and mGluR5 may be—forexample, schizophrenia, and include any disorders known as being relatedto glutamate dysfunction and the modulation of mGluR5. The patient maybe a mammal, preferably a human.

In addition, a person skilled in the art may easily select a specificadministration method and a therapeutically effective amount of thecompound of Chemical Formula (1) or a pharmaceutically acceptable saltthereof with no particular limitations, taking the type of the mammalsto be administered and the disorder, and the specific type of thecompound of Chemical Formula (1) and its activity on positive allostericmodulation of mGluR5.

According to still another aspect, the present disclosure provides amethod of preparing the compound of Chemical Formula (1). Thepreparation of the compound of Chemical Formula (1) may be conducted byusing a known compound or a compound easily prepared therefrom in theperspective of a person skilled in the art regarding a chemicalsynthesis. Therefore, the following explanations about the method ofpreparing the compound of Chemical Formula (1) merely present exemplarymethods and if necessary, the order of the unit operation may beselectively altered and does not limit the scope of the disclosure.

In a general synthesis method, from compound (2) as a starting materiala heterocycle synthesis reaction is carried out with dichloroacetone toobtain imidazopyrimidine or imidazotriazine derivative (3). From thiscompound, a nucleophilic reaction is carried out to obtain compound (4),and then the final compound (1) can be obtained via Suzuki couplingreaction.

In another synthesis method, from compound (2) as a starting materialSuzuki coupling reaction is carried out to obtain compound (5) in whicharyl or heteroaryl is substituted. Then, a heterocycle synthesisreaction is carried out with the obtained compound and dichloroacetoneto obtain imidazopyrimidine or imidazotriazine derivative (6). From thiscompound, a nucleophilic reaction is carried out to obtain the finalcompound (1).

A heterocycle synthesis reaction is carried out with compound (5)obtained in Reaction Scheme 2 and 1-acetoxy-3-chloroacetone to obtaincompound (7), and the obtained compound is then hydrolyzed to obtaincompound (8). An aromatic nucleophilic reaction of compound (8) iscarried out to obtain the final compound (9).

According to the present disclosure, a novel imidazopyrimidine andimidazotriazine derivative, and a pharmaceutically acceptable saltthereof showing excellent effect on positive allosteric modulation ofmetabotropic glutamate receptor subtype 5 (mGluR5) are provided.Therefore, such imidazopyrimidine and imidazotriazine derivative, and apharmaceutically acceptable salt thereof can be effectively used in theprevention or treatment of disorders mediated by glutamate dysfunctionand mGluR5 such as schizophrenia.

In addition, according to the present disclosure, a method of preparingthe novel imidazopyrimidine and imidazotriazine derivative, apharmaceutical composition comprising the same and a method of positiveallosteric modulation of mGluR5 by using the same, and a method for thetreatment of disorders mediated by glutamate dysfunction and mGluR5 areprovided.

EXAMPLES

Hereinafter, the present disclosure is explained in more detail with thefollowing examples. However, it must be understood that the protectionscope of the present disclosure is not limited to the examples.

Example 1: Synthesis of6-(2-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

Example 1-1: Synthesis of 6-bromo-2-chloromethylimidazo[1,2-a]pyrimidine

5-Bromopyrimidin-2-amine (2 g, 11.5 mmol) and 1,3-dichloropropan-2-one(2.9 g, 23 mmol) were dissolved in DMF (20 ml), and then agitated at110° C. for 2 hours. After confirmation of the reaction termination byliquid chromatography, the reaction solution was diluted with ethylacetate and washed three times with water. Then, the solution was driedwith magnesium sulfate and filtrated. This was under reduced pressure,and the resulting solids were washed with ethyl acetate to obtain thetitle compound (amount: 0.85 g, yield: 30%).

Example 1-2: Synthesis of6-bromo-2-phenoxymethylimidazo[1,2-a]pyrimidine

6-Bromo-2-chloromethylimidazo[1,2-a]pyrimidine (2 g, 8.11 mmol) andphenol (1.5 g, 16.23 mmol) were dissolved in DMF (40 ml), and potassiumcarbonate (3.4 g, 24.34 mmol) was added thereto at room temperature.Then, the reaction solution was agitated at 60° C. for 15 hours. Afterconfirmation of the reaction termination by liquid chromatography, thereaction solution was diluted with ethyl acetate and washed three timeswith water. Then, the solution was dried with magnesium sulfate andfiltrated. This was under reduced pressure, and the resulting solidswere washed with ethyl acetate to obtain the title compound (amount: 0.9g, yield: 38%).

Example 1-3: Synthesis of6-(2-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine synthesis

6-Bromo-2-phenoxymethylimidazo[1,2-a]pyrimidine (0.3 g, 0.99 mmol)obtained in Example 1-2 and 2-fluorophenylboronic acid (0.2 g, 1.43mmol) were dissolved in 1,2-dimethoxyethane (8 ml), and[1,1′-bis(diphenylphosphine)ferrocene]dichloropalladium(II) complexdichloromethane (0.2 g, 0.24 mmol) and 2N sodium carbonate aqueoussolution (1.8 ml, 3.6 mmol) were then added thereto at room temperature.Then, the reaction solution was agitated under reflux at 90° C. for 6hours. After confirmation of the reaction termination by liquidchromatography, the reaction solution was diluted with methylenechloride and filtrated by the use of Cellite™. The solution was washedtwice with water, and then dried with magnesium sulfate and filtrated.This was under reduced pressure and purified by column chromatography(methylene chloride:methanol=50:1) to obtain the title compound (amount:0.1 g, yield: 32%).

1H-NMR (CDCl₃, 500 MHz) δ 8.74 (s, 1H), 8.59 (s, 1H), 7.64 (s, 1H), 7.50(m, 1H), 7.45 (m, 1H), 7.32 (m, 3H), 7.23 (m, 1H), 7.03 (m, 2H), 6.98(m, 1H), 5.39 (s, 2H)

Example 2: Synthesis of 2-phenoxymethyl-6-phenylimidazo[1,2-a]pyrimidine

Phenylboronic acid as a starting material was used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.80 (s, 1H), 8.51 (s, 1H), 7.64 (s, 1H), 7.52(m, 3H), 7.45 (m, 2H), 7.31 (m, 2H), 7.04 (m, 2H), 6.97 (m, 1H), 5.38(s, 2H)

Example 3: Synthesis of6-(2,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2,4-Difluoro phenylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.20 (s, 1H), 8.72 (s, 1H), 8.00 (s, 1H),7.76 (m, 1H), 7.49 (m, 1H), 7.30 (m, 3H), 7.07 (d, 2H), 6.95 (t, 1H),5.27 (s, 2H)

Example 4: Synthesis of6-(2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Methoxyphenylboronic acid as a starting material was used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.74 (s, 1H), 8.55 (s, 1H), 7.61 (s, 1H), 7.42(m, 2H), 7.37 (m, 1H), 7.29 (m, 1H), 7.13 (m, 1H), 7.05 (m, 3H), 6.95(m, 1H), 5.40 (s, 2H), 3.87 (s, 3H)

Example 5: Synthesis of6-(2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Methylphenylboronic acid as a starting material was used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.58 (s, 1H), 8.33 (s, 1H), 7.64 (s, 1H), 7.35(m, 5H), 7.25 (m, 1H), 7.06 (d, 2H), 7.00 (m, 1H), 5.42 (s, 2H), 2.33(s, 3H)

Example 6: Synthesis of6-(4-fluoro-2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Fluoro-2-methylphenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.52 (s, 1H), 8.29 (s, 1H), 7.63 (s, 1H), 7.33(m, 2H), 7.21 (m, 1H), 7.06 (m, 3H), 6.99 (m, 2H), 5.41 (s, 2H), 2.31(s, 3H)

Example 7: Synthesis of6-(2,3-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2,3-Difluorophenylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.73 (s, 1H), 8.62 (s, 1H), 7.67 (s, 1H), 7.30(m, 3H), 7.27 (m, 2H), 7.06 (m, 2H), 6.99 (m, 1H), 5.40 (s, 2H)

Example 8: Synthesis of6-(4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Fluorophenylboronic acid as a starting material was used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.75 (s, 1H), 8.54 (s, 1H), 7.66 (d, 1H), 7.51(m, 1H), 7.31 (m, 3H), 7.26 (m, 1H), 7.15 (m, 1H), 7.05 (m, 2H), 6.98(m, 1H), 5.38 (s, 2H)

Example 9: Synthesis of6-(3-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

3-Aminophenylboronic acid as a starting material was used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.15 (s, 1H), 8.77 (s, 1H), 7.95 (s, 1H),7.31 (t, 2H), 7.15 (t, 1H), 7.07 (d, 2H), 6.95 (t, 1H), 6.86 (s, 1H),6.83 (d, 1H), 6.64 (d, 1H), 5.27 (s, 2H), 5.25 (s, 2H)

Example 10: Synthesis of6-(2-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Aminophenylboronic acid as a starting material was used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.67 (s, 1H), 8.48 (s, 1H), 7.62 (s, 1H), 7.33(m, 2H), 7.20 (m, 1H), 7.13 (m, 1H), 7.05 (m, 2H), 6.99 (m, 1H), 6.90(m, 1H), 6.83 (m, 1H), 5.40 (s, 2H)

Example 11: Synthesis of6-(3-amino-6-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

3-Amino-6-methylphenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.93 (s, 1H), 8.50 (s, 1H), 7.94 (s, 1H),7.31 (t, 2H), 7.07 (d, 2H), 7.00 (m, 1H), 6.96 (m, 1H), 6.58 (d, 1H),6.53 (s, 1H), 5.25 (s, 2H), 5.03 (s, 2H), 2.10 (s, 3H)

Example 12: Synthesis of6-(3-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

3-Amino-4-fluorophenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.14 (s, 1H), 8.75 (s, 1H), 7.95 (s, 1H),7.54 (m, 2H), 7.30 (m, 2H), 7.15 (m, 1H), 7.11 (m, 2H), 6.95 (m, 1H),5.35 (s, 2H), 5.24 (s, 2H)

Example 13: Synthesis of6-(3-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

3-Chloro-4-fluorophenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.73 (s, 1H), 8.50 (s, 1H), 7.66 (s, 1H), 7.61(m, 1H), 7.44 (m, 1H), 7.32 (m, 3H), 7.05 (m, 2H), 7.00 (m, 1H), 5.40(s, 2H)

Example 14: Synthesis of6-(2-dimethylaminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Dimethylaminophenylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.04 (s, 1H), 8.73 (s, 1H), 7.95 (s, 1H),7.39 (m, 1H), 7.32 (m, 3H), 7.21 (m, 1H), 7.19 (m, 2H), 6.96 (m, 2H),5.23 (s, 2H), 2.51 (s, 6H)

Example 15: Synthesis of6-(2-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Chloro-4-fluorophenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.08 (s, 1H), 8.59 (s, 1H), 7.98 (s, 1H),7.65 (m, 2H), 7.40 (m, 1H), 7.31 (m, 2H), 7.06 (m, 2H), 6.95 (m, 1H),5.25 (s, 2H)

Example 16: Synthesis of6-(2-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Hydroxyphenylboronic acid as a starting material was used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.64 (s, 1H), 8.55 (s, 1H), 7.45 (s, 1H), 7.25(m, 4H), 7.05 (m, 1H), 6.98 (m, 1H), 6.92 (m, 3H), 5.21 (s, 2H)

Example 17: Synthesis of6-(3-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

3-Hydroxyphenylboronic acid as a starting material was used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.77 (s, 1H), 8.46 (s, 1H), 7.59 (s, 1H), 7.35(m, 1H), 7.26 (m, 2H), 7.07 (m, 2H), 6.99 (m, 2H), 6.90 (m, 2H), 5.35(s, 2H)

Example 18: Synthesis of6-(4-fluoro-2-trifluoromethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Fluoro-2-trifluoromethylphenylboronic acid as a starting material wasused in the same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.05 (s, 1H), 8.49 (s, 1H), 8.00 (s, 1H),7.85 (m, 1H), 7.71 (m, 2H), 7.32 (m, 2H), 7.09 (m, 2H), 6.95 (m, 1H),5.28 (s, 2H)

Example 19: Synthesis of6-(3,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

3,4-Difluorophenylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.33 (s, 1H), 8.91 (s, 1H), 7.94 (m, 2H),7.64 (m, 2H), 7.32 (m, 2H), 7.08 (m, 2H), 6.96 (m, 1H), 5.26 (s, 2H)

Example 20: Synthesis of6-(2-methoxy-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Methoxy-4-fluorophenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.06 (s, 1H), 8.64 (s, 1H), 7.95 (s, 1H),7.51 (t, 1H), 7.31 (t, 2H), 7.12 (m, 1H), 7.06 (d, 2H), 6.95 (m, 2H),5.26 (s, 2H), 3.84 (s, 3H)

Example 21: Synthesis of6-(4-fluoro-3-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Fluoro-3-methoxyphenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.30 (s, 1H), 8.93 (s, 1H), 7.94 (s, 1H),7.56 (m, 1H), 7.35 (m, 4H), 7.08 (m, 2H), 6.95 (m, 1H), 5.26 (s, 2H),3.94 (s, 3H)

Example 22: Synthesis of6-(4-chloro-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Chloro-2-methoxyphenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.66 (s, 1H), 8.54 (s, 1H), 7.62 (s, 1H), 7.29(m, 3H), 7.05 (m, 5H), 5.37 (s, 2H), 3.86 (s, 3H)

Example 23: Synthesis of6-(4-cyano-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Cyano-2-methoxyphenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.70 (s, 1H), 8.63 (s, 1H), 7.66 (s, 1H), 7.49(d, 2H), 7.32 (m, 3H), 7.06 (m, 2H), 7.01 (m, 1H), 5.40 (s, 2H), 3.93(s, 3H)

Example 24: Synthesis of6-(7-fluorobenzo[1,3]dioxol-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

7-Fluorobenzo[1,3]dioxol-4-ylboronic acid as a starting material wasused in the same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.29 (s, 1H), 8.89 (s, 1H), 8.02 (s, 1H),7.30 (m, 3H), 7.06 (m, 3H), 6.95 (m, 1H), 6.26 (s, 2H), 5.25 (s, 2H)

Example 25: Synthesis of6-(4-fluoro-2-hydroxymethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Fluoro-2-hydroxymethylphenylboronic acid as a starting material wasused in the same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.99 (s, 1H), 8.56 (s, 1H), 7.95 (s, 1H),7.43 (m, 2H), 7.32 (m, 2H), 7.27 (m, 1H), 7.06 (m, 2H), 6.95 (m, 1H),5.44 (s, 1H), 5.27 (s, 2H), 4.47 (s, 2H)

Example 26: Synthesis of6-(4-fluoro-2-methylthiophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Fluoro-2-methylthiophenylboronic acid as a starting material was usedin the same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.01 (s, 1H), 8.51 (s, 1H), 7.96 (s, 1H),7.42 (m, 1H), 7.35 (m, 3H), 7.15 (m, 1H), 7.06 (d, 2H), 6.95 (m, 1H),5.27 (s, 2H), 2.47 (s, 3H)

Example 27: Synthesis of6-(2-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Amino-4-fluorophenylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.59 (s, 1H), 8.39 (s, 1H), 7.58 (s, 1H), 7.29(m, 2H), 7.05 (m, 4H), 6.55 (m, 2H), 5.39 (s, 2H), 3.89 (s, 2H)

Example 28: Synthesis of6-(2,4-difluoro-5-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2,4-Difluoro-5-methoxyphenylboronic acid as a starting material was usedin the same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.14 (s, 1H), 8.69 (s, 1H), 7.95 (s, 1H),7.43 (m, 1H), 7.32 (m, 3H), 7.06 (m, 2H), 6.96 (m, 1H), 5.26 (s, 2H),3.81 (s, 3H)

Example 29: Synthesis of6-(2-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

(2-Fluoropyridin-3-yl)boronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.75 (d, 1H), 8.70 (s, 1H), 8.33 (d, 1H), 7.99(m, 1H), 7.69 (s, 1H), 7.41 (m, 1H), 7.32 (m, 2H), 7.05 (m, 2H), 6.95(m, 1H), 5.41 (s, 2H)

Example 30: Synthesis of6-(6-methoxypyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

6-Methoxypyridin-3-ylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.27 (s, 1H), 8.89 (s, 1H), 8.57 (s, 1H),8.10 (m, 1H), 7.94 (s, 1H), 7.30 (m, 2H), 7.08 (m, 2H), 7.00 (m, 1H),6.96 (t, 1H), 5.26 (s, 2H), 3.90 (s, 3H)

Example 31: Synthesis of6-(6-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

6-Fluoropyridin-3-ylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.36 (s, 1H), 8.93 (s, 1H), 8.65 (s, 1H),8.41 (m, 1H), 7.97 (s, 1H), 7.40 (m, 1H), 7.31 (t, 2H), 7.08 (m, 2H),6.95 (t, 1H), 5.27 (s, 2H)

Example 32: Synthesis of6-(4-methylpyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Methylpyridin-3-ylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (CD3OD, 500 MHz) δ 9.47 (s, 1H), 9.15 (s, 1H), 8.95 (m, 1H), 8.88(m, 1H), 8.39 (s, 1H), 8.15 (s, 1H), 7.35 (m, 2H), 7.12 (m, 2H), 7.04(m, 1H), 5.48 (s, 2H), 2.69 (s, 3H)

Example 33: Synthesis of6-(2,6-difluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2,6-Difluoropyridin-3-ylboronic acid as a starting material was used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.28 (s, 1H), 8.78 (s, 1H), 8.49 (q, 1H),8.03 (s, 1H), 7.40 (d, 1H), 7.30 (t, 2H), 7.07 (d, 2H), 6.95 (t, 1H),5.27 (s, 2H)

Example 34: Synthesis of6-(6-chloropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

6-Chloropyridin-3-ylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (CD3OD, 500 MHz) δ 9.58 (s, 1H), 9.37 (s, 1H), 8.82 (s, 1H), 8.32(s, 1H), 8.25 (d, 1H), 7.71 (m, 1H), 7.35 (m, 2H), 7.11 (m, 2H), 7.04(m, 1H), 5.46 (s, 2H)

Example 35: Synthesis of6-(2-fluoropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

2-Fluoropyridin-4-ylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.57 (s, 1H), 9.06 (s, 1H), 8.38 (m, 1H),7.99 (s, 1H), 7.82 (d, 1H), 7.69 (d, 1H), 7.31 (t, 2H), 7.08 (d, 2H),6.95 (t, 1H), 5.28 (s, 2H)

Example 36: Synthesis of6-(3-chloropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

3-Chloropyridin-4-ylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.42 (s, 1H), 8.91 (s, 1H), 8.85 (s, 1H),8.71 (d, 1H), 8.18 (s, 1H), 7.70 (s, 1H), 7.32 (m, 2H), 7.09 (m, 2H),6.97 (m, 1H), 5.35 (s, 2H)

Example 37: Synthesis of6-(4-chlorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

4-Chlorophenylboronic acid as a starting material was used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.33 (s, 1H), 8.91 (s, 1H), 7.96 (s, 1H),7.81 (d, 2H), 7.60 (d, 2H), 7.31 (t, 2H), 7.09 (d, 2H), 6.95 (t, 1H),5.27 (s, 2H)

Example 38: Synthesis of6-(6-fluoro-4-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

6-Fluoro-4-methyl-3-pyridylboronic acid as a starting material was usedin the same manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.49 (s, 1H), 8.35 (s, 1H), 8.09 (s, 1H), 7.66(s, 1H), 7.30 (m, 2H), 7.03 (m, 2H), 6.97 (m, 2H), 5.39 (s, 2H), 2.36(s, 3H)

Example 39: Synthesis of6-(6-fluoro-5-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

6-Fluoro-5-methyl-3-pyridylboronic acid as a starting material was usedin the same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.35 (s, 1H), 8.89 (s, 1H), 8.42 (s, 1H),8.22 (d, 1H), 7.94 (s, 1H), 7.29 (m, 2H), 7.05 (m, 2H), 6.94 (m, 1H),5.27 (s, 2H), 2.35 (s, 3H)

Example 40: Synthesis of6-(5-fluoro-2-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine

5-Fluoro-2-pyridylboronic acid as a starting material was used in thesame manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.60 (s, 1H), 9.20 (s, 1H), 8.71 (s, 1H),8.13 (d, 1H), 8.02 (s, 1H), 7.94 (t, 1H), 7.28 (t, 2H), 7.07 (d, 2H),6.92 (t, 1H), 5.24 (s, 2H)

Example 41: Synthesis of6-(2,4-difluorophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethylimidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethylimidazo[1,2-a]pyrimidine and2,4-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.20 (s, 1H), 8.72 (s, 1H), 8.02 (s, 1H),7.76 (m, 1H), 7.49 (m, 1H), 7.33 (m, 2H), 6.98 (m, 1H), 6.90 (m, 1H),6.76 (m, 1H) 5.28 (s, 2H)

Example 42: Synthesis of6-(4-fluoro-2-methoxyphenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methoxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.68 (s, 1H), 8.52 (s, 1H), 7.61 (s, 1H), 7.30(m, 1H), 7.23 (m, 1H), 6.82 (m, 2H), 6.76 (m, 2H), 6.68 (m, 1H), 5.35(s, 2H), 3.85 (s, 3H)

Example 43: Synthesis of6-(4-fluoro-3-hydroxyphenyl)-2-(3-fluorophenoxymethyl)-imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-3-hydroxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.20 (s, 1H), 8.81 (s, 1H), 7.98 (s, 1H),7.33 (m, 3H), 7.18 (m, 1H), 6.99 (m, 1H), 6.93 (m, 1H), 6.78 (m, 1H),5.28 (s, 2H)

Example 44: Synthesis of6-(2-aminophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and2-aminophenylboronic acid were used in the same manner as in Example 1-3to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.93 (s, 1H), 8.54 (s, 1H), 7.95 (s, 1H),7.31 (m, 1H), 7.10 (m, 2H), 6.98 (m, 1H), 6.92 (m, 1H), 6.79 (m, 2H),6.63 (m, 1H), 5.27 (s, 2H), 5.14 (s, 2H)

Example 45: Synthesis of6-(3-chloropyridin-4-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethylimidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethylimidazo[1,2-a]pyrimidine and3-chloropyridin-4-ylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.27 (s, 1H), 8.81 (s, 1H), 8.72 (s, 1H),8.67 (s, 1H), 8.06 (s, 1H), 7.69 (m, 1H), 7.32 (m, 1H), 6.99 (m, 1H),6.92 (m, 1H), 6.79 (m, 1H), 5.30 (s, 2H)

Example 46: Synthesis of6-(4-methylpyridin-3-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and4-methylpyridin-3-ylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 9.34 (s, 1H), 9.00 (s, 2H), 8.78 (s, 1H), 8.62(s, 1H), 7.73 (s, 1H), 7.32 (m, 2H), 7.06 (m, 2H), 7.01 (m, 1H), 5.42(s, 2H)

Example 47: Synthesis of6-(2,4-difluorophenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethylimidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethylimidazo[1,2-a]pyrimidine and2,4-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.70 (s, 1H), 8.57 (s, 1H), 7.64 (s, 1H), 7.47(m, 1H), 6.99 (m, 6H), 5.35 (s, 2H)

Example 48: Synthesis of6-(4-fluoro-2-methylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.53 (s, 1H), 8.31 (s, 1H), 7.62 (s, 1H), 7.22(m, 2H), 7.09 (m, 1H), 6.99 (m, 4H), 5.36 (s, 2H), 2.32 (s, 3H)

Example 49: Synthesis of6-(3-chloropyridin-4-yl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and3-chloropyridin-4-ylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.79 (s, 1H), 8.68 (m, 2H), 8.62 (m, 1H), 7.69(s, 1H), 7.38 (m, 1H), 6.99 (m, 4H), 5.37 (s, 2H)

Example 50: Synthesis of6-(2,6-dimethylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and2,6-dimethylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.88 (s, 1H), 8.38 (s, 1H), 7.92 (s, 1H),7.26 (m, 1H), 7.20 (m, 2H), 7.10 (m, 4H), 5.25 (s, 2H), 2.07 (s, 6H)

Example 51: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(6-fluoro-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.74 (s, 1H), 8.55 (s, 1H), 8.44 (s, 1H), 7.99(m, 1H), 7.67 (s, 1H), 7.13 (m, 1H), 6.98 (m, 4H), 5.35 (s, 2H)

Example 52: Synthesis of4-[[6-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-2-yl]methoxy]phenol

Benzene-1,4-diol as a starting material was used in the same manner asin Example 1-2 to obtain6-bromo-2-(4-hydroxyphenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-hydroxyphenoxymethyl)imidazo[1,2-a]pyrimidine and4-fluorophenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.27 (s, 1H), 8.95 (s, 1H), 8.88 (s, 1H),7.90 (s, 1H), 7.82 (m, 2H), 7.38 (t, 2H), 6.89 (d, 2H), 6.68 (d, 2H),5.14 (s, 2H)

Example 53: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and4-fluorophenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.28 (s, 1H), 8.89 (s, 1H), 7.94 (s, 1H),7.81 (s, 2H), 7.38 (s, 2H), 7.12 (m, 4H), 5.25 (s, 2H)

Example 54: Synthesis of2-[(3-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and4-fluorophenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.78 (s, 1H), 8.50 (s, 1H), 7.64 (s, 1H), 7.53(m, 2H), 7.25 (m, 2H), 6.84 (m, 1H), 6.77 (m, 1H), 6.68 (m, 1H), 5.37(s, 2H)

Example 55: Synthesis of2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-fluoro-3-hydroxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 10.21 (s, 1H), 9.21 (s, 1H), 8.80 (s, 1H),7.95 (s, 1H), 7.28 (m, 2H), 7.11 (m, 5H), 5.24 (s, 2H)

Example 56: Synthesis of2-[(4-fluorophenoxy)methyl]-6-phenyl-imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine andphenylboronic acid were used in the same manner as in Example 1-3 toobtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.30 (s, 1H), 8.91 (s, 1H), 7.95 (s, 1H),7.78 (d, 2H), 7.55 (t, 2H), 7.46 (m, 1H), 7.12 (m, 4H), 5.25 (s, 2H)

Example 57: Synthesis of5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-fluoro-2-hydroxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 10.5 (s, 1H), 9.10 (s, 1H), 8.70 (s, 1H),7.99 (s, 1H), 7.48 (m, 1H), 7.35 (m, 1H), 7.00 (m, 1H), 6.93 (m, 1H),6.80 (m, 2H), 5.28 (s, 2H)

Example 58: Synthesis of5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-fluoro-2-hydroxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 10.5 (s, 1H), 9.07 (s, 1H), 8.68 (s, 1H),7.94 (s, 1H), 7.45 (m, 1H), 7.08 (m, 4H), 6.78 (m, 2H), 5.22 (s, 2H)

Example 59: Synthesis of6-(4-fluorophenyl)-2-[(2,3,4,5,6-pentadeuteriophenoxy)methyl]imidazo[1,2-a]pyrimidine

2,3,4,5,6-Pentadeuteriophenol as a starting material was used in thesame manner as in Example 1-2 to obtain6-bromo-2-(2,3,4,5,6-pentadeuteriophenoxymethyl)imidazo[1,2-a]pyrimidine.The obtained6-bromo-2-(2,3,4,5,6-pentadeuteriophenoxymethyl)imidazo[1,2-a]pyrimidineand (4-fluorophenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.29 (d, 1H), 8.89 (d, 1H), 7.95 (s, 1H),7.82 (t, 2H), 7.39 (t, 2H), 5.27 (s, 2H)

Example 60: Synthesis of2-[(4-fluorophenoxy)methyl]6-(o-tolyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine ando-tolylboronic acid were used in the same manner as in Example 1-3 toobtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.00 (s, 1H), 8.58 (s, 1H), 7.93 (s, 1H),7.35 (m, 4H), 7.12 (m, 4H), 5.25 (s, 2H), 2.30 (s, 3H)

Example 61: Synthesis of6-(5-fluoro-2-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(5-fluoro-2-methyl-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.04 (s, 1H), 8.59 (s, 1H), 7.94 (s, 1H),7.40 (t, 1H), 7.28 (m, 1H), 7.22 (m, 1H), 7.12 (m, 4H), 5.25 (s, 2H),2.27 (s, 3H)

Example 62: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-fluoro-4-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.57 (s, 1H), 9.05 (s, 1H), 8.38 (d, 1H),7.98 (s, 1H), 7.82 (m, 1H), 7.70 (s, 1H), 7.12 (m, 4H), 5.25 (s, 2H)

Example 63: Synthesis of2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-hydroxyphenyl)boronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.97 (s, 1H), 9.11 (s, 1H), 8.73 (s, 1H),7.96 (s, 1H), 7.42 (d, 1H), 7.25 (m, 1H), 7.11 (m, 4H), 7.00 (m, 2H),5.23 (s, 2H)

Example 64: Synthesis of6-(2-fluoro-4-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-fluoro-4-methyl-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.27 (s, 1H), 8.88 (s, 1H), 7.93 (s, 1H),7.63 (t, 1H), 7.15 (m, 6H), 5.24 (s, 2H), 2.32 (s, 3H)

Example 65: Synthesis of2-[(4-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and[6-(trifluoromethyl)-3-pyridyl]boronic acid were used in the same manneras in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.48 (s, 1H), 9.17 (s, 1H), 9.00 (d, 1H),8.48 (d, 1H), 8.07 (m, 1H), 7.98 (s, 1H), 7.10 (m, 4H), 5.25 (s, 2H)

Example 66: Synthesis of2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-aminophenyl)boronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.92 (s, 1H), 8.48 (s, 1H), 7.90 (s, 1H),7.08 (m, 6H), 6.76 (d, 1H), 6.65 (t, 1H), 5.22 (s, 2H), 5.13 (s, 1H),3.15 (s, 1H)

Example 67: Synthesis of6-(2-chloro-4-fluoro-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-chloro-4-fluoro-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.09 (s, 1H), 8.59 (s, 1H), 7.96 (s, 1H),7.67 (m, 2H), 7.40 (m, 1H), 7.12 (m, 4H), 5.24 (s, 2H)

Example 68: Synthesis of4-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-cyano-2-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.18 (s, 1H), 8.71 (s, 1H), 7.97 (s, 1H),7.70 (s, 2H), 7.58 (m, 1H), 7.10 (m, 4H), 5.25 (s, 2H)

Example 69: Synthesis of6-(4-chloro-2-methoxy-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-chloro-2-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.08 (s, 1H), 8.64 (s, 1H), 7.94 (s, 1H),7.48 (d, 1H), 7.26 (d, 1H), 7.14 (m, 5H), 5.23 (s, 2H), 3.83 (s, 3H)

Example 70: Synthesis of2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(3-amino-4-fluoro-phenyl)boronic acid as a starting material were usedin the same manner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.15 (s, 1H), 8.75 (s, 1H), 7.94 (s, 1H),7.09 (m, 6H), 6.85 (m, 1H), 5.36 (m, 2H), 5.23 (s, 2H)

Example 71: Synthesis of6-(2,6-difluoro-3-pyridyl)-2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2,6-difluoro-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.69 (m, 2H), 8.09 (m, 1H), 7.69 (s, 1H), 7.27(m, 1H), 7.06 (m, 1H), 6.82 (s, 1H), 6.75 (m, 2H), 5.37 (s, 2H)

Example 72: Synthesis of5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methyl-aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(3-amino-4-methyl-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.12 (s, 1H), 8.74 (s, 1H), 7.93 (s, 1H),7.08 (m, 5H), 6.90 (s, 1H), 6.80 (m, 1H), 5.22 (s, 2H), 5.03 (m, 2H),2.08 (s, 3H)

Example 73: Synthesis of4,5-difluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-4,5-difluoro-phenyl)boronic acid were used in the same manneras in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.96 (s, 1H), 8.48 (s, 1H), 7.94 (s, 1H),7.27 (m, 1H), 7.15 (m, 4H), 6.74 (m, 1H), 5.35 (s, 2H), 5.24 (s, 2H)

Example 74: Synthesis of2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-5-methyl-aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-4-methyl-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.88 (s, 1H), 8.46 (s, 1H), 7.90 (s, 1H),7.10 (m, 4H), 6.95 (m, 1H), 6.57 (s, 1H), 6.47 (m, 1H), 5.22 (s, 2H),5.06 (s, 2H), 2.19 (s, 3H)

Example 75: Synthesis of5-chloro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-4-chloro-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.93 (s, 1H), 8.44 (s, 1H), 7.93 (s, 1H),7.10 (m, 5H), 6.80 (s, 1H), 6.64 (d, 1H), 5.48 (s, 2H), 5.24 (s, 2H)

Example 76: Synthesis of2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-5-methyl-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.92 (s, 1H), 8.50 (s, 1H), 7.91 (s, 1H),7.11 (m, 4H), 6.92 (m, 2H), 6.67 (d, 1H), 5.24 (s, 2H), 4.93 (s, 2H),2.17 (s, 3H)

Example 77: Synthesis of5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-4-fluoro-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.90 (s, 1H), 8.43 (s, 1H), 7.93 (s, 1H),7.10 (m, 5H), 6.53 (m, 1H), 6.42 (m, 1H), 5.46 (s, 2H), 5.23 (s, 2H)

Example 78: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(4-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-methyl-3-pyridyl)boronic acid as were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.07 (s, 1H), 8.62 (s, 1H), 8.50 (t, 2H),7.94 (s, 1H), 7.40 (m, 1H), 7.09 (m, 4H), 5.25 (s, 2H), 2.33 (s, 3H)

Example 79: Synthesis of2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-fluoro-4-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.84 (s, 1H), 8.70 (s, 1H), 8.41 (d, 1H), 7.73(s, 1H), 7.44 (d, 1H), 7.26 (m, 1H), 7.18 (s, 1H), 6.85 (d, 1H), 6.76(m, 2H), 5.39 (s, 2H)

Example 80: Synthesis of2-[(3-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and[6-(trifluoromethyl)-3-pyridyl)boronic acid were used in the same manneras in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.98 (s, 1H), 8.82 (s, 1H), 8.66 (s, 1H), 8.12(d, 1H), 7.90 (m, 1H), 7.74 (s, 1H), 6.86 (m, 1H), 6.72 (m, 2H), 5.41(s, 2H)

Example 81: Synthesis of2-[(3-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(6-fluoro-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.74 (s, 1H), 8.54 (s, 1H), 8.44 (s, 1H), 8.00(m, 1H), 7.67 (s, 1H), 7.13 (m, 1H), 6.83 (m, 1H), 6.76 (d, 1H), 6.71(m, 1H), 5.37 (s, 2H)

Example 82: Synthesis of2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-fluoro-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.75 (s, 1H), 8.70 (s, 1H), 8.32 (d, 1H), 7.98(t, 1H), 7.67 (s, 1H), 7.39 (t, 1H), 6.83 (m, 1H), 6.76 (d, 1H), 6.69(m, 1H), 5.37 (s, 2H)

Example 83: Synthesis of6-(5,6-difluoro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(5,6-difluoro-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.40 (s, 1H), 8.94 (s, 1H), 8.55 (m, 1H),8.48 (s, 1H), 7.96 (s, 1H), 7.09 (m, 4H), 5.25 (s, 2H)

Example 84: Synthesis of5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methoxy-aniline

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(3-amino-4-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.08 (s, 1H), 8.74 (s, 1H), 7.91 (s, 1H),7.10 (m, 4H), 6.91 (m, 3H), 5.21 (s, 2H), 4.90 (s, 2H), 3.79 (s, 3H)

Example 85: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(5-fluoro-2-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 9.07 (m, 2H), 8.56 (s, 1H), 7.78 (s, 1H), 7.66(s, 1H), 7.59 (m, 1H), 6.98 (m, 4H), 5.35 (s, 2H)

Example 86: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-2-pyridyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(5-methoxy-2-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.54 (s, 1H), 9.17 (s, 1H), 8.40 (s, 1H),8.00 (m, 2H), 7.56 (d, 1H), 7.10 (m, 4H), 5.22 (s, 2H), 3.88 (s, 3H)

Example 87: Synthesis of6-(4-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-chloro-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.22 (s, 1H), 8.77 (s, 1H), 8.71 (s, 1H),8.64 (d, 1H), 8.02 (s, 1H), 7.77 (d, 1H), 7.12 (m, 4H), 5.28 (s, 2H)

Example 88: Synthesis of6-(5-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(5-chloro-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.46 (s, 1H), 8.99 (d, 2H), 8.70 (s, 1H),8.42 (s, 1H), 7.97 (s, 1H), 7.11 (m, 4H), 5.26 (s, 2H)

Example 89: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-3-pyridyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(5-methoxy-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.38 (s, 1H), 8.96 (s, 1H), 8.55 (s, 1H),8.34 (s, 1H), 7.94 (s, 1H), 7.78 (s, 1H), 7.09 (m, 4H), 5.24 (s, 2H),3.90 (s, 3H)

Example 90: Synthesis of5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-ol

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(6-hydroxy-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.35 (s, 1H), 8.91 (s, 1H), 8.62 (s, 1H),8.39 (m, 1H), 7.95 (s, 1H), 7.38 (d, 1H), 7.11 (m, 4H), 5.22 (s, 2H)

Example 91: Synthesis of6-(6-fluoro-5-methyl-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(6-fluoro-5-methyl-3-pyridyl)boronic acid were used in the same manneras in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.34 (s, 1H), 8.92 (s, 1H), 8.44 (s, 1H),8.25 (d, 1H), 7.95 (s, 1H), 7.10 (m, 4H), 5.25 (s, 2H), 2.32 (s, 3H)

Example 92: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(6-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(6-methyl-3-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.34 (s, 1H), 8.92 (s, 1H), 8.84 (s, 1H),8.06 (d, 1H), 7.95 (s, 1H), 7.41 (d, 1H), 7.10 (m, 4H), 5.25 (s, 2H),2.32 (s, 3H)

Example 93: Synthesis of2-[(3-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(5-fluoro-2-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.61 (s, 1H), 9.18 (s, 1H), 8.69 (s, 1H),8.12 (t, 1H), 8.03 (s, 1H), 7.92 (t, 1H), 7.30 (m, 1H), 6.95 (d, 1H),6.88 (d, 1H), 6.75 (t, 1H), 5.24 (s, 2H)

Example 94: Synthesis of2-[(3-fluorophenoxy)methyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(trifluoromethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.27 (s, 1H), 8.77 (s, 1H), 8.23 (s, 1H),7.89 (t, 1H), 7.76 (t, 1H), 7.68 (t, 1H), 7.35 (m, 1H), 7.01 (d, 1H),6.93 (d, 1H), 6.81 (t, 1H), 5.38 (s, 2H)

Example 95: Synthesis of4-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-cyano-2-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.18 (s, 1H), 8.70 (s, 1H), 7.99 (s, 1H),7.67 (m, 2H), 7.58 (m, 1H), 7.32 (m, 1H), 6.98 (m, 1H), 6.91 (m, 1H),6.78 (m, 1H), 5.28 (s, 2H), 3.88 (s, 3H)

Example 96: Synthesis of[5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(hydroxymethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.98 (s, 1H), 8.55 (s, 1H), 7.95 (s, 1H),7.42 (m, 2H), 7.33 (m, 1H), 7.24 (m, 1H), 6.97 (d, 1H), 6.91 (d, 1H),6.76 (t, 1H), 5.41 (s, 1H), 5.28 (s, 2H) 4.45 (d, 2H)

Example 97: Synthesis of[5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(hydroxymethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.97 (s, 1H), 8.54 (s, 1H), 7.93 (s, 1H),7.41 (m, 2H), 7.24 (m, 1H), 7.10 (m, 4H), 5.74 (s, 1H), 5.23 (s, 2H)4.45 (d, 2H)

Example 98: Synthesis of6-(4-fluoro-2-methylsulfanyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(4-fluoro-2-methylsulfanyl-phenyl)boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.01 (s, 1H), 8.51 (s, 1H), 7.98 (s, 1H),7.43 (t, 1H), 7.28 (d, 1H), 7.12 (m, 5H), 5.26 (s, 2H), 2.48 (s, 3H)

Example 99: Synthesis of2-[(4-fluorophenoxy)methyl]-6-(2-methoxy-4-pyridyl)imidazo[1,2-a]pyrimidine

4-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-methoxy-4-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.80 (s, 1H), 8.60 (s, 1H), 8.30 (s, 1H), 7.66(s, 1H), 6.98 (m, 6H), 5.34 (s, 2H), 4.01 (s, 3H)

Example 100: Synthesis of2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-5-methyl-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.95 (s, 1H), 8.51 (s, 1H), 7.94 (s, 1H),7.33 (m, 1H), 6.98 (m, 1H), 6.93 (m, 3H), 6.79 (t, 1H), 6.68 (d, 1H),5.41 (s, 2H), 4.95 (s, 2H), 2.21 (s, 3H)

Example 101: Synthesis of5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

3-Fluorophenol as a starting material was used in the same manner as inExample 1-2 to obtain6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-4-fluoro-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.91 (s, 1H), 8.44 (s, 1H), 7.93 (s, 1H),7.31 (m, 1H), 7.08 (t, 1H), 6.97 (d, 1H), 6.90 (d, 1H), 6.77 (t, 1H),6.52 (t, 1H), 5.48 (s, 2H), 5.27 (s, 2H)

Example 102: Synthesis of6-(4-fluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine and silver carbonate were used in the same manner asin Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluorophenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.77 (s, 1H), 8.51 (s, 1H), 8.22 (s, 1H), 7.63(m, 4H), 7.25 (m, 2H), 6.83 (m, 2H), 5.67 (s, 2H)

Example 103: Synthesis of6-(2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine and silver carbonate were used in the same manner asin Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and2-methylphenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.58 (s, 1H), 8.33 (s, 1H), 8.23 (s, 1H), 7.65(m, 2H), 7.37 (m, 3H), 7.11 (m, 1H), 6.93 (m, 2H), 5.68 (s, 2H), 2.34(s, 3H)

Example 104: Synthesis of6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methoxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.65 (s, 1H), 8.52 (s, 1H), 8.20 (s, 1H), 7.61(s, 1H), 7.58 (t, 1H), 7.31 (t, 1H), 6.91 (t, 1H), 6.85 (d, 1H), 6.77(m, 2H), 5.63 (s, 2H), 3.84 (s, 3H)

Example 105: Synthesis of6-(2,4-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and2,4-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.59 (s, 1H), 9.19 (s, 1H), 8.35 (s, 1H),8.23 (s, 1H), 7.82 (m, 2H), 7.59 (m, 1H), 7.39 (m, 1H), 7.09 (t, 1H),6.98 (d, 1H), 5.65 (s, 2H)

Example 106: Synthesis of6-(4-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.53 (s, 1H), 8.31 (s, 1H), 8.22 (s, 1H), 7.66(m, 2H), 7.24 (m, 1H), 7.05 (m, 2H), 6.90 (m, 2H), 5.68 (s, 2H), 2.32(s, 3H)

Example 107: Synthesis of6-(2,3-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and2,3-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.69 (d, 2H), 8.19 (s, 1H), 7.70 (s, 1H), 7.61(s, 1H), 7.28 (m, 3H), 6.90 (m, 2H), 5.65 (s, 2H)

Example 108: Synthesis of6-(5-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and5-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.55 (s, 1H), 8.35 (s, 1H), 8.22 (s, 1H), 7.69(s, 1H), 7.62 (m, 1H), 7.30 (m, 1H), 7.10 (m, 1H), 6.99 (d, 1H), 6.92(t, 1H), 6.87 (m, 1H), 5.68 (s, 2H), 2.29 (s, 3H)

Example 109: Synthesis of6-(3-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and3-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.53 (s, 1H), 8.36 (s, 1H), 8.21 (s, 1H), 7.68(s, 1H), 7.61 (m, 1H), 7.28 (m, 1H), 7.15 (t, 1H), 7.08 (t, 1H), 6.91(t, 1H), 6.85 (d, 1H), 5.67 (s, 2H), 2.23 (s, 3H)

Example 110: Synthesis of6-(7-fluoro-2H-benzo[1,3]dioxol-4-yl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and2-(7-fluoro-2H-1,3-benzodioxol-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolanewere used in the same manner as in Example 1-3 to obtain the titlecompound.

1H-NMR (CDCl₃, 500 MHz) δ 8.84 (s, 1H), 8.75 (s, 1H), 8.21 (d, 1H), 7.62(m, 2H), 7.06 (m, 1H), 6.93 (m, 1H), 6.85 (m, 2H), 6.16 (s, 2H), 5.65(s, 2H)

Example 111: Synthesis of6-(4-chloro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and4-chloro-2-methoxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.64 (s, 1H), 8.54 (s, 1H), 8.18 (d, 1H), 7.59(m, 2H), 7.28 (m, 1H), 7.07 (m, 2H), 6.88 (m, 2H), 5.62 (s, 2H), 3.84(s, 3H)

Example 112: Synthesis of6-(3-fluoro-2-methoxy-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(3-fluoro-2-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.73 (d, 1H), 8.62 (d, 1H), 8.22 (t, 1H), 7.67(s, 1H), 7.64 (m, 1H), 7.19 (m, 3H), 6.94 (t, 1H), 6.88 (m, 1H), 5.85(s, 2H), 3.85 (s, 3H)

Example 113: Synthesis of6-[4-fluoro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(trifluoromethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.47 (s, 1H), 8.38 (s, 1H), 8.22 (d, 1H), 7.67(s, 1H), 7.64 (m, 1H), 7.57 (m, 1H), 7.43 (m, 2H), 6.93 (m, 1H), 6.87(m, 1H), 5.67 (s, 2H)

Example 114: Synthesis of6-(4-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(4-fluoro-2-methyl-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.51 (s, 1H), 8.35 (s, 1H), 8.03 (s, 1H), 7.67(s, 1H), 7.38 (m, 1H), 7.22 (t, 1H), 7.04 (m, 2H), 6.83 (m, 1H), 5.61(s, 2H), 2.31 (s, 3H)

Example 115: Synthesis of6-(2-ethylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(2-ethylphenyl)boronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.55 (s, 1H), 8.34 (s, 1H), 8.21 (d, 1H), 7.67(s, 1H), 7.62 (m, 1H), 7.42 (m, 2H), 7.32 (m, 1H), 7.23 (d, 1H), 6.93(t, 1H), 6.87 (d, 1H), 5.67 (s, 2H), 2.63 (q, 2H), 1.15 (t, 3H)

Example 116: Synthesis of6-(4-fluoro-2-methyl-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

4-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(4-fluoro-2-methyl-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.64 (s, 1H), 8.08 (d, 1H), 8.05 (d, 1H), 7.48(t, 2H), 7.40 (m, 2H), 6.91 (m, 1H), 6.59 (s, 1H), 5.47 (s, 2H), 2.47(s, 3H)

Example 117: Synthesis of6-(2-fluoro-4-methyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(2-fluoro-4-methyl-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.64 (s, 1H), 8.08 (d, 1H), 8.05 (d, 1H), 7.48(t, 2H), 7.40 (m, 2H), 6.91 (m, 1H), 6.59 (s, 1H), 5.47 (s, 2H), 2.47(s, 3H)

Example 118: Synthesis of6-(4-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

4-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(4-fluoro-2-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.67 (s, 1H), 8.49 (s, 1H), 8.16 (d, 1H), 7.61(s, 1H), 7.31 (m, 1H), 6.78 (m, 2H), 6.69 (m, 1H), 6.55 (d, 1H), 5.65(s, 2H), 3.85 (s, 3H)

Example 119: Synthesis of2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(trifluoromethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.48 (s, 1H), 8.35 (s, 1H), 8.02 (s, 1H), 7.63(s, 1H), 7.55 (d, 1H), 7.39 (m, 3H), 6.83 (m, 1H), 5.60 (s, 2H)

Example 120: Synthesis of6-(2,4-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

4-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(2,4-difluorophenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.71 (s, 1H), 8.59 (s, 1H), 8.17 (d, 1H), 7.68(s, 1H), 7.50 (m, 1H), 7.08 (m, 2H), 6.73 (m, 1H), 6.58 (m, 1H), 5.69(s, 2H)

Example 121: Synthesis of6-(3-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

4-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(3-fluoro-2-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.72 (s, 1H), 8.61 (s, 1H), 8.16 (s, 1H), 7.64(s, 1H), 7.17 (m, 3H), 6.70 (m, 1H), 6.55 (m, 1H), 5.66 (s, 2H), 3.84(s, 3H)

Example 122: Synthesis of6-(2,3-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

4-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(2,3-difluorophenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.77 (s, 1H), 8.68 (s, 1H), 8.19 (s, 1H), 7.72(s, 1H), 7.30 (m, 3H), 6.74 (m, 1H), 6.59 (m, 1H), 5.70 (s, 2H)

Example 123: Synthesis of6-(4-fluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

4-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(4-fluorophenyl)boronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.81 (s, 1H), 8.53 (s, 1H), 8.19 (s, 1H), 7.69(m, 1H), 7.57 (m, 2H), 7.29 (m, 2H), 6.74 (m, 1H), 6.59 (m, 1H), 5.70(s, 2H)

Example 124: Synthesis of6-(3-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(3-fluoro-2-methyl-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.50 (s, 1H), 8.41 (s, 1H), 8.00 (s, 1H), 7.68(s, 1H), 7.37 (m, 1H), 7.29 (m, 1H), 7.16 (m, 1H), 7.04 (m, 1H), 6.81(m, 1H), 5.58 (s, 2H), 2.21 (s, 3H)

Example 125: Synthesis of2-[(4-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

4-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(trifluoromethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.48 (s, 1H), 8.36 (s, 1H), 8.17 (m, 1H), 7.65(m, 1H), 7.57 (m, 1H), 7.41 (m, 2H), 6.72 (m, 1H), 6.56 (m, 1H), 5.67(s, 2H)

Example 126: Synthesis of2-[(5-fluoro-2-pyridyl)oxymethyl]-6-(o-tolyl)imidazo[1,2-a]pyrimidine

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine ando-tolylboronic acid were used in the same manner as in Example 1-3 toobtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.56 (s, 1H), 8.30 (s, 1H), 8.02 (s, 1H), 7.62(m, 1H), 7.37 (m, 3H), 7.25 (m, 2H), 6.83 (m, 1H), 5.60 (s, 2H), 2.31(s, 3H)

Example 127: Synthesis of6-(4-chloro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(4-chloro-2-methyl-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.49 (s, 1H), 8.29 (s, 1H), 8.01 (s, 1H), 7.62(s, 1H), 7.37 (m, 2H), 7.28 (m, 1H), 7.17 (m, 1H), 6.80 (m, 1H), 5.59(s, 2H), 2.27 (s, 3H)

Example 128: Synthesis of6-(2,4-dimethylphenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(2,4-dimethylphenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.54 (s, 1H), 8.29 (s, 1H), 8.03 (s, 1H), 7.62(s, 1H), 7.38 (m, 1H), 7.16 (s, 1H), 7.13 (m, 2H), 6.82 (m, 1H), 5.60(s, 2H), 2.39 (s, 3H), 2.28 (s, 3H)

Example 129: Synthesis of6-(4-fluorophenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(4-fluorophenyl)boronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.27 (s, 1H), 8.88 (d, 1H), 8.20 (d, 1H),7.91 (s, 1H), 7.83 (m, 2H), 7.74 (m, 1H), 7.38 (m, 2H), 6.97 (m, 1H),5.47 (s, 2H)

Example 130: Synthesis of2-(2-pyridyloxymethyl)-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and[6-(trifluoromethyl)-3-pyridyl]boronic acid were used in the same manneras in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.95 (s, 1H), 8.77 (s, 1H), 8.63 (s, 1H), 8.19(s, 1H), 8.09 (d, 1H), 7.86 (s, 1H), 7.73 (s, 1H), 7.61 (s, 1H), 6.86(m, 2H), 5.67 (s, 2H)

Example 131: Synthesis of2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and[6-(trifluoromethyl)-3-pyridyl]boronic acid were used in the same manneras in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.96 (s, 1H), 8.80 (s, 1H), 8.64 (s, 1H), 8.10(m, 1H), 7.88 (m, 1H), 7.73 (s, 1H), 7.61 (m, 1H), 7.51 (m, 1H), 6.85(m, 1H), 5.64 (s, 2H)

Example 132: Synthesis of6-(5-fluoro-2-pyridyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(5-fluoro-2-pyridyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.58 (s, 1H), 9.17 (s, 1H), 8.69 (s, 1H),8.20 (s, 1H), 8.12 (t, 1H), 7.98 (s, 1H), 7.92 (t, 1H), 7.71 (t, 1H),6.99 (t, 1H), 6.87 (d, 1H), 5.47 (s, 2H)

Example 133: Synthesis of2-fluoro-5-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(3-amino-4-fluoro-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.74 (s, 1H), 8.45 (s, 1H), 8.03 (s, 1H), 7.63(s, 1H), 7.38 (t, 1H), 7.12 (m, 1H), 6.95 (m, 1H), 6.84 (m, 2H), 5.64(s, 2H), 3.92 (s, 2H)

Example 134: Synthesis of2-fluoro-5-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]aniline

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(3-amino-4-fluoro-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.73 (s, 1H), 8.44 (s, 1H), 8.21 (s, 1H), 7.62(m, 2H), 7.11 (m, 1H), 6.92 (m, 4H), 5.65 (s, 2H), 3.92 (s, 2H)

Example 135: Synthesis of[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(hydroxymethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.96 (s, 1H), 8.54 (s, 1H), 8.20 (d, 1H),7.89 (s, 1H), 7.75 (t, 1H), 7.40 (m, 2H), 7.24 (m, 1H), 7.00 (m, 1H),6.89 (d, 1H), 5.49 (s, 2H), 5.40 (m, 1H), 4.45 (d, 2H)

Example 136: Synthesis of3-methoxy-4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(4-cyano-2-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.66 (s, 1H), 8.60 (s, 1H), 8.18 (d, 1H), 7.64(s, 1H), 7.60 (m, 1H), 7.47 (d, 1H), 7.40 (d, 1H), 7.26 (d, 1H), 6.90(m, 1H), 6.84 (m, 1H), 5.63 (s, 1H), 3.89 (s, 3H)

Example 137: Synthesis of4-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and(4-cyano-2-methoxy-phenyl)boronic acid were used in the same manner asin Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.16 (s, 1H), 8.69 (s, 1H), 8.17 (s, 1H),7.93 (s, 1H), 7.72 (m, 3H), 7.58 (m, 1H), 6.95 (m, 1H), 5.45 (s, 2H),3.88 (s, 3H)

Example 138: Synthesis of6-(4-fluoro-2-methylsulfanyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(4-fluoro-2-methylsulfanyl-phenyl)boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.99 (s, 1H), 8.51 (s, 1H), 8.22 (d, 1H),7.94 (s, 1H), 7.76 (m, 1H), 7.41 (m, 1H), 7.28 (d, 1H), 7.15 (t, 1H),7.01 (t, 1H), 6.90 (d, 1H), 5.51 (s, 2H), 2.48 (s, 3H)

Example 139: Synthesis of[5-fluoro-2-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol

5-Fluoropyridin-2-ol as a starting material and silver carbonate wereused in the same manner as in Example 1-2 to obtain6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(hydroxymethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.99 (s, 1H), 8.54 (s, 1H), 8.21 (s, 1H),7.89 (s, 1H), 7.71 (t, 1H), 7.43 (m, 2H), 7.22 (t, 1H), 6.97 (d, 1H),5.46 (s, 2H), 5.41 (s, 1H), 4.45 (s, 2H)

Example 140: Synthesis of4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(4-cyanophenyl)boronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.81 (s, 1H), 8.60 (s, 1H), 8.22 (s, 1H), 7.85(d, 2H), 7.71 (t, 3H), 7.63 (m, 1H), 6.95 (m, 1H), 6.89 (m, 1H), 5.69(s, 2H)

Example 141: Synthesis of6-[4-fluoro-2-(methoxymethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(methoxymethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.95 (s, 1H), 8.52 (s, 1H), 8.20 (t, 1H),7.91 (s, 1H), 7.74 (m, 1H), 7.48 (m, 1H), 7.36 (m, 1H), 7.31 (m, 1H),7.02 (m, 1H), 6.88 (d, 1H), 5.49 (s, 2H), 4.37 (s, 2H), 3.23 (s, 3H)

Example 142: Synthesis of[2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-5-(trifluoromethyl)phenyl]methanol

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and[2-(hydroxymethyl)-4-(trifluoromethyl)phenyl]boronic acid were used inthe same manner as in Example 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.63 (s, 1H), 8.55 (d, 1H), 8.20 (d, 1H), 7.89(s, 1H), 7.72 (d, 1H), 7.63 (m, 2H), 7.49 (d, 1H), 6.93 (t, 1H), 6.85(d, 1H), 5.63 (s, 2H), 4.72 (s, 2H)

Example 143: Synthesis of6-(2-isopropylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and(2-isopropylphenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.92 (s, 1H), 8.46 (s, 1H), 8.20 (s, 1H),7.90 (s, 1H), 7.73 (t, 1H), 7.45 (m, 2H), 7.28 (t, 2H), 7.02 (t, 1H),6.89 (d, 1H), 5.50 (s, 2H), 2.93 (m, 1H), 1.14 (d, 6H)

Example 144: Synthesis of4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-3-(trifluoromethyl)benzaldehyde

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and[4-formyl-2-(trifluoromethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 10.18 (s, 1H), 9.10 (s, 1H), 8.53 (s, 1H),8.40 (s, 1H), 8.29 (d, 1H), 8.19 (d, 1H), 7.95 (s, 1H), 7.87 (d, 1H),7.74 (t, 1H), 7.02 (t, 1H), 6.90 (d, 1H), 5.51 (s, 2H)

Example 145: Synthesis of6-[4-chloro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

2-Hydroxypyridine as a starting material and silver carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and[4-chloro-2-(trifluoromethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.38 (s, 1H), 8.91 (s, 1H), 8.31 (s, 1H),8.23 (d, 1H), 8.07 (s, 1H), 7.98 (d, 1H), 7.80 (t, 1H), 7.65 (d, 1H),7.09 (t, 1H), 6.95 (d, 1H), 5.63 (s, 2H)

Example 146: Synthesis of6-(4-fluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Hydroxypyridine as a starting material and cesium carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluorophenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.79 (s, 1H), 8.53 (s, 1H), 8.46 (s, 1H), 8.25(s, 1H), 7.68 (s, 1H), 7.55 (m, 2H), 7.39 (m, 1H), 7.25 (m, 3H), 5.43(s, 2H)

Example 147: Synthesis of6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Hydroxypyridine as a starting material and cesium carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methoxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.70 (s, 1H), 8.52 (s, 1H), 8.46 (s, 1H), 8.27(s, 1H), 7.63 (s, 1H), 7.35 (m, 2H), 7.24 (m, 1H), 6.84 (m, 2H), 5.43(s, 2H), 3.87 (s, 3H)

Example 148: Synthesis of6-(2,4-difluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Hydroxypyridine as a starting material and cesium carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and2,4-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.71 (s, 1H), 8.60 (s, 1H), 8.46 (s, 1H), 8.27(s, 1H), 7.68 (s, 1H), 7.50 (m, 1H), 7.38 (m, 1H), 7.26 (m, 1H), 7.08(m, 2H), 5.43 (s, 2H)

Example 149: Synthesis of6-(4-fluoro-2-methylphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Hydroxypyridine as a starting material and cesium carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.50 (s, 1H), 8.38 (d, 2H), 8.23 (s, 1H), 7.67(s, 1H), 7.36 (m, 1H), 7.21 (m, 2H), 7.03 (m, 2H), 5.39 (s, 2H), 2.30(s, 3H)

Example 150: Synthesis of6-(4-fluoro-2-hydroxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Hydroxypyridine as a starting material and cesium carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-hydroxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.21 (s, 1H), 8.75 (s, 1H), 8.45 (s, 1H),8.19 (s, 1H), 7.98 (s, 1H), 7.55 (m, 1H), 7.45 (m, 1H), 7.34 (m, 1H),6.62 (s, 2H), 5.34 (s, 2H), 4.05 (m, 1H)

Example 151: Synthesis of6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

4-Hydroxypyridine as a starting material and cesium carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methoxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.68 (s, 1H), 8.54 (s, 1H), 8.43 (s, 2H), 7.61(s, 1H), 7.29 (m, 1H), 6.95 (d, 2H), 6.79 (m, 2H), 5.39 (s, 2H), 3.84(s, 3H)

Example 152: Synthesis of6-(2,4-difluorophenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

4-Hydroxypyridine as a starting material and cesium carbonate were usedin the same manner as in Example 1-2 to obtain6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine. The obtained6-bromo-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine and2,4-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.68 (s, 1H), 8.62 (s, 1H), 8.45 (m, 2H), 7.67(s, 1H), 7.47 (m, 1H), 7.06 (m, 1H), 7.02 (m, 1H), 6.95 (m, 2H), 5.39(s, 2H)

Example 153: Synthesis of6-(2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and2-methylphenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.62 (s, 1H), 8.36 (s, 1H), 8.31 (s, 1H), 8.16(s, 1H), 7.66 (s, 1H), 7.38 (m, 4H), 7.19 (m, 1H), 5.44 (s, 2H), 2.35(s, 3H)

Example 154: Synthesis of6-(4-fluoro-2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.55 (s, 1H), 8.36 (s, 1H), 8.29 (s, 1H), 8.14(s, 1H), 7.67 (s, 1H), 7.23 (m, 1H), 7.17 (m, 1H), 7.04 (m, 2H), 5.42(s, 2H), 3.32 (s, 3H)

Example 155: Synthesis of6-(4-fluoro-2-methoxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methoxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.71 (s, 1H), 8.52 (s, 1H), 8.29 (s, 1H), 8.14(s, 1H), 7.62 (s, 1H), 7.33 (m, 1H), 7.16 (m, 1H), 6.82 (m, 2H), 5.41(s, 2H), 3.87 (s, 3H)

Example 156: Synthesis of6-(4-fluoro-2-hydroxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-hydroxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 10.52 (s, 1H), 9.10 (s, 1H), 8.71 (s, 1H),8.31 (s, 1H), 8.20 (s, 1H), 8.03 (s, 1H), 7.65 (m, 1H), 7.47 (m, 1H),6.80 (m, 2H), 5.38 (s, 2H)

Example 157: Synthesis of6-(2,4-difluorophenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

6-Fluoro-3-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and2,4-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.73 (s, 1H), 8.59 (s, 1H), 7.99 (s, 1H), 7.67(s, 1H), 7.50 (m, 2H), 7.07 (m, 2H), 6.90 (m, 1H), 5.40 (s, 2H)

Example 158: Synthesis of6-(4-fluoro-2-methylphenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.56 (s, 1H), 8.34 (s, 1H), 7.99 (s, 1H), 7.65(s, 1H), 7.53 (m, 1H), 7.25 (m, 1H), 7.11 (m, 1H), 7.07 (m, 1H), 6.89(m, 1H), 5.41 (s, 2H), 2.33 (s, 3H)

Example 159: Synthesis of6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-3-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.17 (s, 1H), 8.79 (s, 1H), 8.17 (s, 1H),7.94 (m, 1H), 7.80 (s, 1H), 7.44 (t, 1H), 7.38 (m, 1H), 7.30 (m, 1H),7.21 (m, 1H), 5.50 (s, 2H), 2.34 (s, 3H)

Example 160: Synthesis of6-(4-fluoro-2-methylphenyl)-2-(5-chloropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine

5-Chloro-3-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-chloropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-chloropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.56 (d, 1H), 8.35 (s, 2H), 8.24 (s, 1H), 7.66(s, 1H), 7.40 (s, 1H), 7.25 (m, 1H), 7.05 (m, 2H), 5.42 (s, 2H), 2.33(s, 3H)

Example 161: Synthesis of6-(2,4-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and2,4-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.20 (s, 1H), 8.73 (s, 1H), 8.04 (s, 1H),7.99 (d, 1H), 7.68 (m, 1H), 7.41 (m, 1H), 7.22 (m, 1H), 6.97 (m, 1H),6.86 (s, 1H), 5.35 (s, 2H)

Example 162: Synthesis of6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methylphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound. 1H-NMR (CDCl₃, 500 MHz) δ 8.53(s, 1H), 8.29 (s, 1H), 8.04 (d, 1H), 7.60 (s, 1H), 7.20 (t, 1H), 7.03(d, 1H), 7.00 (t, 1H), 6.86 (m, 1H), 6.54 (s, 1H), 5.40 (s, 2H), 2.29(s, 3H)

Example 163: Synthesis of6-(4-fluoro-2-methoxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-methoxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.69 (s, 1H), 8.54 (s, 1H), 8.04 (s, 1H), 7.62(s, 1H), 7.32 (m, 1H), 6.87 (d, 1H), 6.78 (m, 2H), 6.55 (s, 1H), 5.40(s, 2H), 3.85 (s, 3H)

Example 164: Synthesis of6-(4-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluorophenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.80 (s, 1H), 8.51 (s, 1H), 8.07 (d, 1H), 7.65(s, 1H), 7.54 (m, 2H), 7.24 (m, 2H), 6.88 (s, 1H), 6.57 (s, 1H), 5.43(s, 2H)

Example 165: Synthesis of6-(2,3-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and2,3-difluorophenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.78 (s, 1H), 8.68 (s, 1H), 8.08 (s, 1H), 7.70(s, 1H), 7.29 (s, 3H), 6.89 (s, 1H), 6.58 (s, 1H), 5.44 (s, 2H)

Example 166: Synthesis of6-(2-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and2-fluorophenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.79 (s, 1H), 8.64 (s, 1H), 8.07 (s, 1H), 7.65(s, 1H), 7.51 (m, 1H), 7.47 (m, 1H), 7.34 (m, 2H), 6.88 (s, 1H), 6.57(s, 1H), 5.43 (s, 2H)

Example 167: Synthesis of6-(4-fluoro-2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-hydroxyphenylboronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.53 (s, 1H), 9.19 (s, 1H), 8.42 (s, 1H),8.13 (s, 1H), 7.55 (m, 2H), 7.10 (s, 1H), 7.01 (m, 2H), 6.86 (m, 1H),5.59 (s, 2H)

Example 168: Synthesis of6-(2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and2-methylphenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.61 (s, 1H), 8.35 (s, 1H), 8.07 (s, 1H), 7.63(s, 1H), 7.39 (m, 4H), 6.88 (s, 1H), 6.58 (s, 1H), 5.44 (s, 2H), 2.34(s, 3H)

Example 169: Synthesis of6-(2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and2-hydroxyphenylboronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.14 (s, 1H), 8.76 (s, 1H), 8.07 (m, 2H),7.43 (m, 1H), 7.25 (m, 1H), 7.06 (m, 1H), 7.00 (m, 1H), 6.95 (m, 2H),5.40 (s, 2H)

Example 170: Synthesis of6-(4-fluoro-2-hydroxymethylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and4-fluoro-2-hydroxymethylphenylboronic acid were used in the same manneras in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.03 (s, 1H), 8.60 (s, 1H), 8.09 (s, 1H),8.04 (s, 1H), 7.42 (m, 2H), 7.26 (m, 1H), 7.07 (d, 1H), 6.97 (s, 1H),5.43 (s, 2H), 4.48 (m, 2H), 4.11 (m, 1H)

Example 171: Synthesis of6-(4-fluorophenyl)-2-[(5-fluoro-3-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and(4-fluorophenyl)boronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.30 (s, 1H), 8.91 (s, 1H), 8.32 (s, 1H),8.20 (s, 1H), 8.02 (s, 1H), 7.82 (t, 2H), 7.66 (d, 1H), 7.39 (t, 2H),5.39 (s, 2H)

Example 172: Synthesis of2-[(2-chloro-4-pyridyl)oxymethyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine

2-Chloro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-chloropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-chloropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and(4-fluorophenyl)boronic acid were used in the same manner as in Example1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.30 (s, 1H), 8.91 (s, 1H), 8.24 (d, 1H),8.01 (s, 1H), 7.83 (m, 2H), 7.39 (t, 2H), 7.30 (s, 1H), 7.15 (m, 1H),5.42 (s, 2H)

Example 173: Synthesis of2-[(5-fluoro-3-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(trifluoromethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.08 (s, 1H), 8.51 (s, 1H), 8.32 (m, 1H),8.21 (m, 1H), 7.98 (m, 1H), 7.88 (m, 1H), 7.70 (m, 2H), 7.65 (m, 1H),5.40 (s, 2H)

Example 174: Synthesis of2-[(2-fluoro-4-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

2-Fluoro-4-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(trifluoromethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.35 (s, 1H), 8.83 (s, 1H), 8.33 (s, 1H),8.09 (d, 1H), 7.88 (m, 1H), 7.77 (m, 1H), 7.67 (m, 1H), 7.07 (d, 1H),6.98 (s, 1H), 5.59 (s, 2H)

Example 175: Synthesis of5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-4-fluoro-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.92 (s, 1H), 8.45 (s, 1H), 8.29 (s, 1H),8.18 (s, 1H), 7.97 (s, 1H), 7.64 (d, 1H), 7.08 (t, 1H), 6.52 (d, 1H),6.43 (m, 1H), 5.47 (s, 2H), 5.37 (s, 2H)

Example 176: Synthesis of5-fluoro-2-[2-[(2-fluoro-4-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine and(2-amino-4-fluoro-phenyl)boronic acid were used in the same manner as inExample 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.92 (s, 1H), 8.45 (s, 1H), 8.05 (d, 1H),7.98 (s, 1H), 7.06 (m, 2H), 6.93 (s, 1H), 6.52 (d, 1H), 6.42 (t, 1H),5.47 (m, 2H), 5.40 (s, 2H)

Example 177: Synthesis of[5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol

3-Fluoro-5-hydroxypyridine as a starting material and cesium carbonatewere used in the same manner as in Example 1-2 to obtain6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine. Theobtained6-bromo-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine and[4-fluoro-2-(hydroxymethyl)phenyl]boronic acid were used in the samemanner as in Example 1-3 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.01 (s, 1H), 8.56 (s, 1H), 8.30 (s, 1H),8.21 (s, 1H), 8.02 (s, 1H), 7.64 (d, 1H), 7.40 (m, 2H), 7.22 (t, 1H),5.41 (s, 1H), 5.40 (s, 2H), 4.46 (s, 2H)

Example 178: Synthesis of2-(2,4-difluorophenyl)-6-(phenoxymethyl)imidazo[1,2-b][1,2,4]triazine

Example 178-1: Synthesis of 6-bromo-1,2,4-triazine-3-amine

1,2,4-Triazine-3-amine (2 g, 20.814 mmol) was dissolved in acetonitrile(20.8 ml) and water (31.5 ml). After the reaction temperature was cooledto 0° C., N-bromosuccinimide (3.89 g, 20.855 mmol) was added thereto.The resulting mixture was agitated for 10 minutes, and then heated toroom temperature and agitated.

After the reaction termination, the resulting mixture was diluted withethyl acetate and cooled to 0° C. Sodium carbonate was added thereto,agitated for 10 minutes, and washed with saturated sodium bicarbonateand brine. After drying with anhydrous magnesium sulfate and filtration,the solvent was concentrated under reduced pressure to obtain6-bromo-1,2,4-triazine-3-amine (amount: 2.4 g, yield: 67%).

Example 178-2: Synthesis of6-(2,4-difluorophenyl)-1,2,4-triazine-3-amine

6-Bromo-1,2,4-triazine-3-amine (0.5 g, 2.857 mmol),2,4-difluorophenylboronic acid (0.68 g, 4.286 mmol), 2N sodium carbonateand [1,1′-bis(diphenylphosphine)ferrocene]dichloropalladium(II) complexwith dichloromethane (0.28 g, 0.343 mmol) were added to1,2-dimethoxyethane (28.6 ml) and agitated at 90° C. overnight. Afterthe temperature of the reaction mixture was cooled to room temperature,the reaction mixture was filtrated with Cellite™ pad, and the solventwas concentrated under reduced pressure, and then washed with ethylacetate and filtrated to obtain yellow solid,6-(2,4-difluorophenyl)-1,2,4-triazine-3-amine (amount: 0.82 g, yield:46%).

Example 178-3: Synthesis of6-(chloromethyl)-2-(2,4-difluorophenyl)imidazo[1,2-b][1,2,4]triazine

6-(2,4-Difluorophenyl)-1,2,4-triazine-3-amine (0.2 g, 0.961 mmol) wasdissolved in dimethylformamide (4.8 ml), and 1,3-dichloroacetone (0.24g, 1.922 mmol) was added thereto and agitated at 110° C. for 2 hours.After the reaction termination, water and ethyl acetate were addedthereto and extracted. After drying with anhydrous magnesium sulfate andfiltration, the solvent was concentrated under reduced pressure. Flashcolumn chromatography was carried out to obtain yellow solid,6-(chloromethyl)-2-(2,4-difluorophenyl)imidazo[1,2-b][1,2,4]triazine(amount: 80 mg, yield: 30%).

Example 178-4: Synthesis of2-(2,4-difluorophenyl)-6-phenoxymethylimidazo[1,2-b][1,2,4]triazine

6-(Chloromethyl)-2-(2,4-difluorophenyl)imidazo[1,2-b][1,2,4]triazine (20mg, 0.071 mmol) was dissolved in dimethylformamide (1 ml), and phenol(14 mg, 0.143 mmol) and potassium carbonate (69 mg, 0.213 mmol) wereadded thereto and agitated at 60° C. for 2 hours. After the reactiontermination, the resulting mixture was filtrated and the solvent wasconcentrated under reduced pressure. Flash column chromatography wascarried out to obtain white solid,2-(2,4-difluorophenyl)-6-phenoxymethylimidazo[1,2-b][1,2,4]triazine(amount: 12 mg, yield: 50%).

1H-NMR (CDCl₃, 500 MHz) δ 8.86 (s, 1H), 8.06 (s, 1H), 7.90 (m, 1H), 7.33(m, 2H), 7.12 (m, 1H), 7.05 (m, 3H), 7.00 (m, 1H), 5.43 (s, 2H)

Example 179: Synthesis of2-(2,4-difluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine

6-(Chloromethyl)-2-(2,4-difluorophenyl)imidazo[1,2-b][1,2,4]triazine (66mg, 0.235 mmol) obtained in Example 178-3 was dissolved indimethylformamide (2.35 ml), and 4-hydroxypyridine (27 mg, 0.282 mmol)and cesium carbonate (0.23 g, 0.705 mmol) were added thereto andagitated at 40° C. for 2 hours. After the reaction termination, theresulting mixture was filtrated with Cellite™ pad, and the solvent wasconcentrated under reduced pressure. Column chromatography was carriedout to obtain the title compound (amount: 10 mg, yield: 11%).

1H-NMR (CDCl₃, 500 MHz) δ 8.88 (s, 1H), 8.50 (m, 2H), 8.05 (s, 1H), 7.89(m, 1H), 7.09 (m, 2H), 6.99 (s, 2H), 5.49 (s, 2H)

Example 180: Synthesis of2-(2,4-difluorophenyl)-6-((pyridin-2-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine

6-(Chloromethyl)-2-(2,4-difluorophenyl)imidazo[1,2-b][1,2,4]triazine (90mg, 0.321 mmol) obtained in Example 178-3 was dissolved indimethylformamide (3.2 ml), and 2-hydroxypyridine (37 mg, 0.385 mmol)and silver carbonate were added thereto and agitated at 40° C. for 2hours. After the reaction termination, the resulting mixture wasfiltrated with Cellite™ pad, and the solvent was concentrated underreduced pressure. Column chromatography was carried out to obtain thetitle compound (amount: 23 mg, yield: 19%).

1H-NMR (CDCl₃, 500 MHz) δ 8.85 (s, 1H), 8.22 (s, 1H), 8.08 (s, 1H), 7.91(m, 1H), 7.64 (m, 1H), 7.10 (m, 2H), 6.93 (m, 2H), 5.72 (s, 2H)

Example 181: Synthesis of2-(4-fluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine

(4-Fluorophenyl)boronic acid as a starting material was used in the samemanner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(4-fluorophenyl)imidazo[1,2-b][1,2,4]triazine. Theobtained6-(chloromethyl)-2-(4-fluorophenyl)imidazo[1,2-b][1,2,4]triazine wasused in the same manner as in Example 180 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.85 (s, 1H), 8.20 (s, 1H), 8.04 (S, 1H), 7.98(m, 2H), 7.62 (t, 1H), 7.28 (m, 2H), 6.92 (m, 1H), 6.86 (m, 1H), 5.69(s, 2H)

Example 182: Synthesis of2-(2-methylphenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine

(2-Methylphenyl)boronic acid as a starting material was used in the samemanner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(2-methylphenyl)imidazo[1,2,-b][1,2,4]triazine. Theobtained6-(chloromethyl)-2-(2-methylphenyl)imidazo[1,2,-b][1,2,4]triazine wasused in the same manner as in Example 180 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.56 (s, 1H), 8.20 (s, 1H), 8.04 (s, 1H), 7.62(m, 1H), 7.46 (m, 2H), 7.36 (m, 2H), 6.91 (m, 1H), 6.86 (m, 1H), 5.70(s, 2H), 2.43 (s, 3H)

Example 183: Synthesis of2-(2,4-difluorophenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine

6-(Chloromethyl)-2-(2,4-difluorophenyl)imidazo[1,2-b][1,2,4]triazineobtained in Example 178-3 as a starting material and2-fluoro-4-hydroxypyridine were used in the same manner as in Example179 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.89 (s, 1H), 8.07 (m, 2H), 7.91 (m, 1H), 7.12(m, 1H), 7.06 (m, 1H), 6.89 (s, 1H), 6.57 (s, 1H), 5.46 (s, 2H)

Example 184: Synthesis of2-(4-fluoro-2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine

(4-Fluoro-2-methyl-phenyl)boronic acid as a starting material was usedin the same manner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(4-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazine.The obtained6-(chloromethyl)-2-(4-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazineand 2-fluoro-4-hydroxypyridine were used in the same manner as inExample 179 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.59 (s, 1H), 8.09 (t, 1H), 8.02 (d, 1H), 7.45(m, 1H), 7.10 (m, 2H), 6.89 (m, 1H), 6.58 (d, 1H), 5.44 (s, 2H), 2.47(s, 3H)

Example 185: Synthesis of2-(2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine

(2-Methylphenyl)boronic acid as a starting material was used in the samemanner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(o-tolyl)imidazo[1,2-b][1,2,4]triazine. The obtained6-(chloromethyl)-2-(o-tolyl)imidazo[1,2-b][1,2,4]triazine and2-fluoro-4-hydroxypyridine were used in the same manner as in Example179 to obtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.64 (s, 1H), 8.08 (d, 1H), 8.05 (d, 1H), 7.48(t, 2H), 7.40 (m, 2H), 6.91 (m, 1H), 6.59 (s, 1H), 5.47 (s, 2H), 2.47(s, 3H)

Example 186: Synthesis of2-[4-fluoro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine

[4-Fluoro-2-(trifluoromethyl)phenyl]boronic acid as a starting materialwas used in the same manner as in Example 178-2 and Example 178-3 toobtain6-(chloromethyl)-2-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-b][1,2,4]triazine.The obtained6-(chloromethyl)-2-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-b][1,2,4]triazineand 2-hydroxypyridine were used in the same manner as in Example 180 toobtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.52 (s, 1H), 8.21 (d, 1H), 8.07 (s, 1H), 7.61(m, 3H), 7.46 (m, 1H), 6.94 (m, 1H), 6.89 (d, 1H), 5.73 (s, 2H)

Example 187: Synthesis of2-(3-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine

(3-Fluoro-2-methyl-phenyl)boronic acid as a starting material was usedin the same manner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(3-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazine.The obtained6-(chloromethyl)-2-(3-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazineand 2-hydroxypyridine were used in the same manner as in Example 180 toobtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.78 (s, 1H), 8.41 (s, 1H), 8.22 (d, 1H),7.76 (t, 1H), 7.44 (s, 2H), 7.40 (m, 1H), 7.03 (t, 1H), 6.91 (t, 1H),5.55 (s, 2H), 2.30 (s, 3H)

Example 188: Synthesis of2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine

(4-Fluoro-2-methyl-phenyl)boronic acid as a starting material was usedin the same manner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(4-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazine.The obtained6-(chloromethyl)-2-(4-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazineand 2-hydroxypyridine were used in the same manner as in Example 180 toobtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.77 (s, 1H), 8.39 (s, 1H), 8.22 (d, 1H),7.76 (m, 1H), 7.64 (m, 1H), 7.30 (m, 1H), 7.24 (t, 1H), 7.03 (t, 1H),6.91 (d, 1H), 5.55 (s, 2H), 2.43 (s, 3H)

Example 189: Synthesis of2-[4-chloro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine

[4-Chloro-2-(trifluoromethyl)phenyl]boronic acid as a starting materialwas used in the same manner as in Example 178-2 and Example 178-3 toobtain6-(chloromethyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]imidazo[1,2-b][1,2,4]triazine.The obtained6-(chloromethyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]imidazo[1,2-b][1,2,4]triazineand 2-hydroxypyridine were used in the same manner as in Example 180 toobtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.51 (s, 1H), 8.21 (d, 1H), 8.06 (s, 1H), 7.87(s, 1H), 7.73 (d, 1H), 7.63 (t, 1H), 7.53 (d, 1H), 6.94 (t, 1H), 6.88(d, 1H), 5.72 (s, 2H)

Example 190: Synthesis of2-(4-chloro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine

(4-Chloro-2-methyl-phenyl)boronic acid as a starting material was usedin the same manner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(4-chloro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazine.The obtained6-(chloromethyl)-2-(4-chloro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazineand 2-hydroxypyridine were used in the same manner as in Example 180 toobtain the title compound.

1H-NMR (CDCl₃, 500 MHz) δ 8.55 (s, 1H), 8.22 (d, 1H), 8.07 (s, 1H), 7.65(m, 1H), 7.41 (m, 3H), 6.95 (m, 1H), 6.89 (m, 1H), 5.72 (s, 2H), 2.45(s, 3H)

Example 191: Synthesis of2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine

(4-Fluoro-2-methyl-phenyl)boronic acid as a starting material was usedin the same manner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(4-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazine.The obtained6-(chloromethyl)-2-(4-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazineand 6-fluoropyridin-2-ol were used in the same manner as in Example 180to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.78 (s, 1H), 8.42 (s, 1H), 7.93 (t, 1H),7.65 (t, 1H), 7.30 (m, 1H), 7.24 (m, 1H), 6.87 (m, 1H), 6.77 (m, 1H),5.50 (s, 2H), 2.42 (s, 3H)

Example 192: Synthesis of2-(4-fluoro-2-methyl-phenyl)-6-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine

(4-Fluoro-2-methyl-phenyl)boronic acid as a starting material was usedin the same manner as in Example 178-2 and Example 178-3 to obtain6-(chloromethyl)-2-(4-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazine.The obtained6-(chloromethyl)-2-(4-fluoro-2-methyl-phenyl)imidazo[1,2-b][1,2,4]triazineand 5-fluoropyridin-2-ol were used in the same manner as in Example 180to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.77 (s, 1H), 8.39 (s, 1H), 8.19 (s, 1H),7.74 (m, 1H), 7.63 (m, 1H), 7.31 (m, 1H), 7.24 (m, 1H), 6.98 (m, 1H),5.52 (s, 2H), 2.42 (s, 3H)

Example 193: Synthesis of[5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate

[5-Fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol(100 mg, 0.27 mmol) obtained in Example 97 was dissolved indimethylformamide (5 ml), and 1,1′-carbonyldiimidazole (88 mg, 0.54mmol) was added thereto and agitated at room temperature for 30 minutes.Ammonia water (5 ml) was added to this solution and agitated at roomtemperature for 4 hours. Ethyl acetate was added to the reactionsolution and extracted. After drying with anhydrous magnesium sulfateand filtration, the solvent was concentrated under reduced pressure.Flash column chromatography was carried out to obtain the title compound(amount: 88 mg, yield: 80%).

1H-NMR (DMSO-d6, 500 MHz) δ 9.00 (s, 1H), 8.55 (s, 1H), 7.94 (s, 1H),7.49 (t, 1H), 7.36 (m, 2H), 7.09 (m, 4H), 6.70 (m, 2H), 5.25 (s, 2H),4.94 (s, 2H), 3.32 (s, 3H)

Example 194: Synthesis of[5-fluoro-2-[2-(phenoxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate

[5-Fluoro-2-[2-(phenoxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanolobtained in Example 25 was used in the same manner as in Example 193 toobtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 9.01 (s, 1H), 8.56 (s, 1H), 7.96 (s, 2H),7.52 (m, 1H), 7.37 (m, 4H), 7.09 (m, 2H), 6.98 (m, 1H), 6.67 (m, 1H),6.56 (m, 1H), 5.29 (s, 2H), 4.95 (s, 1H)

Example 195: Synthesis of[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate

[5-Fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanolobtained in Example 135 was used in the same manner as in Example 193 toobtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.99 (s, 1H), 8.55 (s, 1H), 8.22 (d, 1H),7.91 (s, 1H), 7.77 (m, 1H), 7.50 (m, 1H), 7.37 (m, 2H), 7.04 (m, 1H),6.92 (m, 1H), 6.68 (m, 1H), 6.57 (m, 1H), 5.52 (s, 2H), 4.95 (s, 2H)

Example 196: Synthesis of[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylacetate

[5-Fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol(100 mg, 0.29 mmol) obtained in Example 135 was dissolved indimethylformamide (5 ml), and trimethylamine (58 mg, 0.57 mmol) andacetyl chloride (31 mg, 0.4 mmol) were added thereto at 0° C. andagitated at room temperature for 2 hours. After the reactiontermination, water and ethyl acetate were added to the reaction solutionand extracted. After drying ethyl acetate solution with anhydrousmagnesium sulfate and filtration, the solvent was concentrated underreduced pressure. Flash column chromatography was carried out to obtainthe title compound (amount: 57 mg, yield: 50%).

1H-NMR (DMSO-d6, 500 MHz) δ 8.96 (s, 1H), 8.51 (s, 1H), 8.20 (t, 1H),7.90 (s, 1H), 7.73 (t, 1H), 7.48 (t, 1H), 7.41 (m, 1H), 7.36 (m, 1H),7.01 (t, 1H), 6.89 (d, 1H), 5.49 (s, 2H), 5.03 (s, 2H), 1.98 (s, 3H)

Example 197: Synthesis of6-[2-(chloromethyl)-4-fluoro-phenyl]-2-[(4-fluorophenoxy)methyl)imidazo[1,2-a]pyrimidine

[5-Fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol(100 mg, 0.27 mmol) obtained in Example 97 was dissolved indimethylformamide (5 ml), and trimethylamine (58 mg, 0.57 mmol) andmethanesulfonyl chloride (65 mg, 0.57 mmol) were added thereto at 0° C.and agitated at room temperature for 2 hours. Ethyl acetate and waterwere added to the reaction solution and extracted. The ethyl acetatesolution was dried with anhydrous magnesium sulfate and filtrated, andthe solvent was concentrated under reduced pressure. Flash columnchromatography was carried out to obtain the title compound (amount: 73mg, yield: 70%).

1H-NMR (DMSO-d6, 500 MHz) δ 9.00 (s, 1H), 8.54 (s, 1H), 7.95 (s, 1H),7.50 (m, 2H), 7.38 (m, 1H), 7.12 (m, 4H), 5.24 (s, 2H), 4.74 (s, 2H)

Example 198: Synthesis of6-[4-fluoro-2-(fluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine

[5-Fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol(100 mg, 0.29 mmol) obtained in Example 135 was dissolved in methylenechloride (10 ml), and diethylaminosulfur trifluoride (70 mg, 0.44 mmol)was added thereto at 0° C. and agitated at room temperature for 30minutes. Saturated ammonium chloride aqueous solution was added to thereaction solution and extracted by the use of methylene chloride andwater. The methylene chloride extract solution was dried with anhydrousmagnesium sulfate and filtrated, and the solvent was concentrated underreduced pressure. Flash column chromatography was carried out to obtainthe title compound (amount: 92 mg, yield: 90%).

1H-NMR (DMSO-d6, 500 MHz) δ 8.97 (s, 1H), 8.52 (s, 1H), 8.21 (m, 1H),7.93 (s, 1H), 7.77 (m, 1H), 7.54 (m, 2H), 7.45 (m, 1H), 7.05 (m, 1H),6.89 (m, 1H), 5.51 (s, 2H), 5.48 (s, 1H), 5.39 (s, 1H)

Example 199: Synthesis of6-[4-fluoro-2-(fluoromethyl)phenyl]-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine

[5-Fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanolobtained in Example 97 as a starting material was used in the samemanner as in Example 198 to obtain the title compound.

1H-NMR (DMSO-d6, 500 MHz) δ 8.98 (s, 1H), 8.54 (s, 1H), 7.97 (s, 1H),7.57 (m, 2H), 7.44 (m, 1H), 7.12 (m, 4H), 5.49 (s, 1H), 5.39 (s, 1H),5.26 (s, 2H)

Experimental Example: Pharmacological Activity Test

Efficacy as a positive allosteric modulator (PAM) of mGluR5 of thecompounds of the Examples was tested as follows:

Calcium Influx Assay Based on Fluorescence

Ca²⁺ (calcium) influx assay is an experiment for measuring the activityof a positive allosteric modulator of mGluR5 receptor in which humanmGluR5 receptor-overexpressed HEK293 cell line is used. The day beforethe experiment, cells were prepared in a cell culture medium (DMEM, 5%FBS) with the density of 80,000/well, and 100 μl of cells were dispensedinto each well of a poly-D-lysine-coated 96-well plate. Cells wereincubated in a 5% CO₂, 37° C. incubator. The next day, the cell culturemedium was removed from the plate, and 100 μl of 1× Fluo-4 calciumindicator diluted with a buffer (1× Hank's balanced salt solution, 20 mMHEPES, 2.5 mM probenecid) were added to each well and incubated at 37°C. for 1 hour. The compound stock solutions were prepared in 100% DMSO,and the compounds were serially diluted with a ¼ dilution to 6 or 7concentrations (final concentration was 10 μM to 10 nM). The dilutedcompound solutions were added to the plate with 0.1 to 0.2% of finalDMSO concentration. 1 hour after the addition of Fluo-4 calciumindicator, L-glutamate (EC₂₀ concentration) and the test compoundsolutions were added to the plate, and Ca²⁺ reaction was then measuredby FLIPR at room temperature. The activity of the compounds wasstandardized on the basis of the results of maximum value-minimum valueof fluorescent reaction, and the activity value was calculated on thebasis that no activity on glutamate EC₂O is 0% and the reaction toglutamate maximum value is 100%.

In the same manner as in the above assay, the efficacy of the testcompounds as a human mGluR5 positive allosteric modulator was calculatedto EC₅₀ and is represented in Table 1 (+: 500-1,000 nM, ++: 100-500 nM,+++: 100 nM or less).

TABLE 1 Human mGluR5 PAM Example EC₅₀ (nM) 1 ++ 2 ++ 3 +++ 4 ++ 5 +++ 6+++ 7 ++ 8 ++ 9 + 10 ++ 11 ++ 12 + 13 + 14 ++ 15 ++ 16 + 17 + 18 ++ 19 +20 ++ 21 + 22 + 23 ++ 24 ++ 25 +++ 26 ++ 27 ++ 28 + 29 ++ 30 + 31 ++ 32++ 33 ++ 34 ++ 35 ++ 36 ++ 37 + 38 ++ 39 ++ 40 ++ 41 ++ 42 + 43 ++ 44 ++45 ++ 46 ++ 47 ++ 48 ++ 49 + 50 + 51 ++ 52 ++ 53 ++ 54 ++ 55 ++ 56 ++ 57++ 58 ++ 59 ++ 60 ++ 61 + 62 + 63 ++ 64 + 65 ++ 66 ++ 67 +++ 68 ++ 69 ++70 ++ 71 ++ 72 ++ 73 + 74 ++ 75 ++ 76 ++ 77 ++ 78 ++ 79 ++ 80 +++ 81 ++82 ++ 83 ++ 84 + 85 ++ 86 ++ 87 + 88 ++ 89 + 90 ++ 91 +++ 92 ++ 93 ++ 94++ 95 ++ 96 ++ 97 ++ 98 ++ 99 + 100 + 101 ++ 102 ++ 103 ++ 104 ++ 105 ++106 ++ 107 + 108 + 109 ++ 110 ++ 111 ++ 112 ++ 113 ++ 114 ++ 115 ++ 116+++ 117 ++ 118 ++ 119 ++ 120 ++ 121 ++ 122 + 123 ++ 124 ++ 125 ++ 126 ++127 ++ 128 + 129 + 130 ++ 131 ++ 132 +++ 133 + 134 ++ 135 ++ 136 + 137++ 138 ++ 139 + 140 ++ 141 ++ 142 ++ 143 + 144 + 145 ++ 146 + 147 +148 + 149 ++ 150 + 151 ++ 152 ++ 153 ++ 154 ++ 155 ++ 156 ++ 157 + 158++ 159 + 160 + 161 ++ 162 +++ 163 ++ 164 ++ 165 ++ 166 ++ 167 ++ 168 +++169 ++ 170 ++ 171 ++ 172 ++ 173 + 174 ++ 175 + 176 ++ 177 + 178 ++ 179++ 180 ++ 181 + 182 ++ 183 ++ 184 ++ 185 ++ 186 ++ 187 ++ 188 +++ 189 +190 ++ 191 + 192 ++ 193 ++ 194 ++ 195 ++ 196 ++ 197 ++ 198 +++ 199 ++

1.-21. (canceled)
 22. A method for preparing a compound of Formula (1)comprising: carrying out a heterocycle synthesis reaction with acompound of Formula (2) as a starting material in dichloroacetone toobtain a compound of Formula (3); carrying out a nucleophilic reactionwith the compound of Formula (3) to obtain a compound of Formula (4);and carrying out Suzuki coupling reaction with the compound of Formula(4) to obtain the compound of Formula (1),

wherein X is CH or N; Z is O or S; R₁ is aryl optionally substitutedwith one or more substituents selected from halo, hydroxy, alkyl,alkoxy, alkylthio, amino, dialkylamino, cyano, formyl, haloalkyl,hydroxyalkyl, alkoxyalkyl, carbamoyloxy alkyl, alkyl-C(O)O-alkyl,dialkylaminoalkyl and 5- or 6-membered heterocycloalkylalkyl; or 5- to12-membered, unsaturated heterocyclyl optionally substituted with one ormore substituents selected from halo, hydroxy, alkyl, alkoxy andhaloalkyl; and R₂ is aryl optionally substituted with one or moresubstituents selected from halo, deuterium, hydroxy and alkyl; or 5- to12-membered, unsaturated heterocyclyl optionally substituted with one ormore substituents selected from halo and alkyl.
 23. The method accordingto claim 22, wherein R₁ is selected from the group consisting of:

wherein n is 0, 1, 2, 3 or 4; each R₃ is selected from halo, hydroxy,C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino,cyano, formyl, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅alkyl, carbamoyloxy-C₁-C₅ alkyl, C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl, di(C₁-C₅alkyl)amino-C₁-C₅ alkyl and 5- or 6-membered heterocycloalkyl-C₁-C₅alkyl; and each R₄ is selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅alkoxy and halo-C₁-C₅ alkyl; and R₂ is selected from the groupconsisting of:

wherein m is 0, 1, 2, 3 or 4; R₅ is selected from halo, deuterium,hydroxy and C₁-C₅ alkyl; and R₆ is selected from halo and C₁-C₅ alkyl.24. The method according to claim 22, wherein R₁ is phenyl optionallysubstituted with 1 to 3 substituents selected from halo, hydroxy, C₁-C₅alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino,cyano, formyl, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅alkyl, carbamoyloxy-C₁-C₅ alkyl and C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl; or 5-to 10-membered, unsaturated heterocyclyl having 1-3 heteroatoms selectedfrom N, O and S, which is optionally substituted with 1 to 3substituents selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy andhalo-C₁-C₅ alkyl.
 25. The method according to claim 22, wherein R₂ isphenyl optionally substituted with 1 to 5 substituents selected fromhalo, deuterium, hydroxy and C₁-C₅ alkyl; or 5- or 6-membered heteroarylhaving 1 to 3 heteroatoms selected from N, O and S, which is optionallysubstituted with 1 to 3 substituents selected from halo and C₁-C₅ alkyl.26. The method according to according to claim 22, wherein X is CH; Z isO; R₁ is phenyl optionally substituted with 1 to 3 substituents selectedfrom halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino,halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl and C₁-C₅ alkoxy-C₁-C₅ alkyl; andR₂ is pyridyl optionally substituted with 1 or 2 substituents selectedfrom halo and C₁-C₅ alkyl.
 27. The method according to according toclaim 22, wherein the compound of Formula (1) is selected from the groupconsisting of:6-(2-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;2-phenoxymethyl-6-phenylimidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-amino-6-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-dimethylaminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-trifluoromethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methoxy-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-3-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-chloro-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-cyano-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(7-fluorobenzo[1,3]dioxol-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxymethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylthiophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,4-difluoro-5-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-methoxypyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-methylpyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,6-difluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-chloropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-fluoropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-chlorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoro-4-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoro-5-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(5-fluoro-2-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-3-hydroxyphenyl)-2-(3-fluorophenoxymethyl)-imidazo[1,2-a]pyrimidine;6-(2-aminophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-methylpyridin-3-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(2,6-dimethylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;4-[[6-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-2-yl]methoxy]phenol;2-[(4-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;2-[(4-fluorophenoxy)methyl]-6-phenyl-imidazo[1,2-a]pyrimidine;5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;6-(4-fluorophenyl)-2-[(2,3,4,5,6-pentadeuteriophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]6-(o-tolyl)imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;6-(2-fluoro-4-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(2-chloro-4-fluoro-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;4-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;6-(4-chloro-2-methoxy-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(2,6-difluoro-3-pyridyl)-2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methyl-aniline;4,5-difluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-5-methyl-aniline;5-chloro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[(4-fluorophenoxy)methyl]-6-(4-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;6-(5,6-difluoro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methoxy-aniline;2-[(4-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-2-pyridyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;6-(5-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-3-pyridyl)imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-ol;6-(6-fluoro-5-methyl-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(6-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;4-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;[5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;[5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;6-(4-fluoro-2-methylsulfanyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(2-methoxy-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(4-fluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(7-fluoro-2H-benzo[1,3]dioxol-4-yl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methoxy-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-[4-fluoro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2-ethylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methyl-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2-fluoro-4-methyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(4-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-(o-tolyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-dimethylphenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-(2-pyridyloxymethyl)-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-pyridyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-fluoro-5-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]aniline;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;3-methoxy-4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;4-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;6-(4-fluoro-2-methylsulfanyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;[5-fluoro-2-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;6-[4-fluoro-2-(methoxymethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;[2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-5-(trifluoromethyl)phenyl]methanol;6-(2-isopropylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-3-(trifluoromethyl)benzaldehyde;6-[4-chloro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(5-chloropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxymethylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(5-fluoro-3-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(2-chloro-4-pyridyl)oxymethyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-[(5-fluoro-3-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;2-[(2-fluoro-4-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;5-fluoro-2-[2-[(2-fluoro-4-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;[5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;2-(2,4-difluorophenyl)-6-(phenoxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((pyridin-2-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2-methylphenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-[4-fluoro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(3-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-[4-chloro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-chloro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-[(6-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine;[5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(phenoxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylacetate;6-[2-(chloromethyl)-4-fluoro-phenyl]-2-[(4-fluorophenoxy)methyl)imidazo[1,2-a]pyrimidine;6-[4-fluoro-2-(fluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;and6-[4-fluoro-2-(fluoromethyl)phenyl]-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine.28. A method for preparing a compound of Formula (1) comprising:carrying out Suzuki coupling reaction with a compound of Formula (2) asa starting material to obtain a compound of Formula (5); carrying out aheterocycle synthesis reaction with the compound of Formula (5) anddichloroacetone to obtain a compound of Formula (6); and carrying out anucleophilic reaction with the compound of Formula (6) to obtain thecompound of Formula (1),

wherein X is CH or N; Z is O or S; R₁ is aryl optionally substitutedwith one or more substituents selected from halo, hydroxy, alkyl,alkoxy, alkylthio, amino, dialkylamino, cyano, formyl, haloalkyl,hydroxyalkyl, alkoxyalkyl, carbamoyloxy alkyl, alkyl-C(O)O-alkyl,dialkylaminoalkyl and 5- or 6-membered heterocycloalkylalkyl; or 5- to12-membered, unsaturated heterocyclyl optionally substituted with one ormore substituents selected from halo, hydroxy, alkyl, alkoxy andhaloalkyl; and R₂ is aryl optionally substituted with one or moresubstituents selected from halo, deuterium, hydroxy and alkyl; or 5- to12-membered, unsaturated heterocyclyl optionally substituted with one ormore substituents selected from halo and alkyl.
 29. The method accordingto claim 28, wherein R₁ is selected from the group consisting of:

wherein n is 0, 1, 2, 3 or 4; each R₃ is selected from halo, hydroxy,C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino,cyano, formyl, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅alkyl, carbamoyloxy-C₁-C₅ alkyl, C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl, di(C₁-C₅alkyl)amino-C₁-C₅ alkyl and 5- or 6-membered heterocycloalkyl-C₁-C₅alkyl; and each R₄ is selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅alkoxy and halo-C₁-C₅ alkyl; and R₂ is selected from the groupconsisting of:

wherein m is 0, 1, 2, 3 or 4; R₅ is selected from halo, deuterium,hydroxy and C₁-C₅ alkyl; and R₆ is selected from halo and C₁-C₅ alkyl.30. The method according to claim 28, wherein R₁ is phenyl optionallysubstituted with 1 to 3 substituents selected from halo, hydroxy, C₁-C₅alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino,cyano, formyl, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅alkyl, carbamoyloxy-C₁-C₅ alkyl and C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl; or 5-to 10-membered, unsaturated heterocyclyl having 1-3 heteroatoms selectedfrom N, O and S, which is optionally substituted with 1 to 3substituents selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy andhalo-C₁-C₅ alkyl.
 31. The method according to claim 28, R₂ is phenyloptionally substituted with 1 to 5 substituents selected from halo,deuterium, hydroxy and C₁-C₅ alkyl; or 5- or 6-membered heteroarylhaving 1 to 3 heteroatoms selected from N, O and S, which is optionallysubstituted with 1 to 3 substituents selected from halo and C₁-C₅ alkyl.32. The method according to according to claim 28, wherein X is CH; Z isO; R₁ is phenyl optionally substituted with 1 to 3 substituents selectedfrom halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino,halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl and C₁-C₅ alkoxy-C₁-C₅ alkyl; andR₂ is pyridyl optionally substituted with 1 or 2 substituents selectedfrom halo and C₁-C₅ alkyl.
 33. The method according to according toclaim 28, wherein the compound of Formula (1) is selected from the groupconsisting of:6-(2-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;2-phenoxymethyl-6-phenylimidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-amino-6-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-dimethylaminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-trifluoromethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methoxy-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-3-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-chloro-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-cyano-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(7-fluorobenzo[1,3]dioxol-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxymethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylthiophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,4-difluoro-5-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-methoxypyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-methylpyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,6-difluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-chloropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-fluoropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-chlorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoro-4-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoro-5-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(5-fluoro-2-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-3-hydroxyphenyl)-2-(3-fluorophenoxymethyl)-imidazo[1,2-a]pyrimidine;6-(2-aminophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-methylpyridin-3-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(2,6-dimethylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;4-[[6-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-2-yl]methoxy]phenol;2-[(4-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;2-[(4-fluorophenoxy)methyl]-6-phenyl-imidazo[1,2-a]pyrimidine;5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;6-(4-fluorophenyl)-2-[(2,3,4,5,6-pentadeuteriophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]6-(o-tolyl)imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;6-(2-fluoro-4-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(2-chloro-4-fluoro-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;4-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;6-(4-chloro-2-methoxy-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(2,6-difluoro-3-pyridyl)-2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methyl-aniline;4,5-difluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-5-methyl-aniline;5-chloro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[(4-fluorophenoxy)methyl]-6-(4-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;6-(5,6-difluoro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methoxy-aniline;2-[(4-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-2-pyridyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;6-(5-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-3-pyridyl)imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-ol;6-(6-fluoro-5-methyl-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(6-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;4-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;[5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;[5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;6-(4-fluoro-2-methylsulfanyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(2-methoxy-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(4-fluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(7-fluoro-2H-benzo[1,3]dioxol-4-yl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methoxy-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-[4-fluoro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2-ethylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methyl-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2-fluoro-4-methyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(4-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-(o-tolyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-dimethylphenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-(2-pyridyloxymethyl)-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-pyridyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-fluoro-5-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]aniline;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;3-methoxy-4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;4-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;6-(4-fluoro-2-methylsulfanyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;[5-fluoro-2-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;6-[4-fluoro-2-(methoxymethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;[2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-5-(trifluoromethyl)phenyl]methanol;6-(2-isopropylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-3-(trifluoromethyl)benzaldehyde;6-[4-chloro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(5-chloropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxymethylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(5-fluoro-3-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(2-chloro-4-pyridyl)oxymethyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-[(5-fluoro-3-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;2-[(2-fluoro-4-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;5-fluoro-2-[2-[(2-fluoro-4-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;[5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;2-(2,4-difluorophenyl)-6-(phenoxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((pyridin-2-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2-methylphenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-[4-fluoro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(3-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-[4-chloro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-chloro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-[(6-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine;[5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(phenoxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylacetate;6-[2-(chloromethyl)-4-fluoro-phenyl]-2-[(4-fluorophenoxy)methyl)imidazo[1,2-a]pyrimidine;6-[4-fluoro-2-(fluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;and6-[4-fluoro-2-(fluoromethyl)phenyl]-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine.34. A method for preparing a compound of Formula (9) comprising:carrying out a heterocycle synthesis reaction with a compound of Formula(5) and 1-acetoxy-3-chloroacetone to obtain a compound of Formula (7);hydrolyzing the compound of Formula (7) to obtain a compound of Formula(8); and carrying out an aromatic nucleophilic reaction with thecompound of Formula (8) to obtain the compound of Formula (9),

wherein X is CH or N; R₁ is aryl optionally substituted with one or moresubstituents selected from halo, hydroxy, alkyl, alkoxy, alkylthio,amino, dialkylamino, cyano, formyl, haloalkyl, hydroxyalkyl,alkoxyalkyl, carbamoyloxy alkyl, alkyl-C(O)O-alkyl, dialkylaminoalkyland 5- or 6-membered heterocycloalkylalkyl; or 5- to 12-membered,unsaturated heterocyclyl optionally substituted with one or moresubstituents selected from halo, hydroxy, alkyl, alkoxy and haloalkyl;and R₂ is aryl optionally substituted with one or more substituentsselected from halo, deuterium, hydroxy and alkyl; or 5- to 12-membered,unsaturated heterocyclyl optionally substituted with one or moresubstituents selected from halo and alkyl.
 35. The method according toclaim 34, wherein R₁ is selected from the group consisting of:

wherein n is 0, 1, 2, 3 or 4; each R₃ is selected from halo, hydroxy,C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino,cyano, formyl, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅alkyl, carbamoyloxy-C₁-C₅ alkyl, C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl, di(C₁-C₅alkyl)amino-C₁-C₅ alkyl and 5- or 6-membered heterocycloalkyl-C₁-C₅alkyl; and each R₄ is selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅alkoxy and halo-C₁-C₅ alkyl; and R₂ is selected from the groupconsisting of:

wherein m is 0, 1, 2, 3 or 4; R₅ is selected from halo, deuterium,hydroxy and C₁-C₅ alkyl; and R₆ is selected from halo and C₁-C₅ alkyl.36. The method according to claim 34, wherein R₁ is phenyl optionallysubstituted with 1 to 3 substituents selected from halo, hydroxy, C₁-C₅alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino, di(C₁-C₅ alkyl)amino,cyano, formyl, halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkoxy-C₁-C₅alkyl, carbamoyloxy-C₁-C₅ alkyl and C₁-C₅ alkyl-C(O)O—C₁-C₅ alkyl; or 5-to 10-membered, unsaturated heterocyclyl having 1-3 heteroatoms selectedfrom N, O and S, which is optionally substituted with 1 to 3substituents selected from halo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy andhalo-C₁-C₅ alkyl.
 37. The method according to claim 34, wherein R₂ isphenyl optionally substituted with 1 to 5 substituents selected fromhalo, deuterium, hydroxy and C₁-C₅ alkyl; or 5- or 6-membered heteroarylhaving 1 to 3 heteroatoms selected from N, O and S, which is optionallysubstituted with 1 to 3 substituents selected from halo and C₁-C₅ alkyl.38. The method according to according to claim 34, wherein X is CH; R₁is phenyl optionally substituted with 1 to 3 substituents selected fromhalo, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkylthio, amino,halo-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl and C₁-C₅ alkoxy-C₁-C₅ alkyl; andR₂ is pyridyl optionally substituted with 1 or 2 substituents selectedfrom halo and C₁-C₅ alkyl.
 39. The method according to according toclaim 34, wherein the compound of Formula (9) is selected from the groupconsisting of:6-(2-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;2-phenoxymethyl-6-phenylimidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-aminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-amino-6-methylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-dimethylaminophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-chloro-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-hydroxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-trifluoromethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3,4-difluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-methoxy-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-3-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-chloro-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-cyano-2-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(7-fluorobenzo[1,3]dioxol-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxymethylphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylthiophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-amino-4-fluorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,4-difluoro-5-methoxyphenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-methoxypyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-methylpyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,6-difluoropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-chloropyridin-3-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2-fluoropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(4-chlorophenyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoro-4-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(6-fluoro-5-methyl-3-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(5-fluoro-2-pyridyl)-2-phenoxymethylimidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-3-hydroxyphenyl)-2-(3-fluorophenoxymethyl)-imidazo[1,2-a]pyrimidine;6-(2-aminophenyl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-methylpyridin-3-yl)-2-(3-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(3-chloropyridin-4-yl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;6-(2,6-dimethylphenyl)-2-(4-fluorophenoxymethyl)imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;4-[[6-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-2-yl]methoxy]phenol;2-[(4-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;2-[(4-fluorophenoxy)methyl]-6-phenyl-imidazo[1,2-a]pyrimidine;5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;6-(4-fluorophenyl)-2-[(2,3,4,5,6-pentadeuteriophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]6-(o-tolyl)imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenol;6-(2-fluoro-4-methyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(2-chloro-4-fluoro-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;4-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;6-(4-chloro-2-methoxy-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(2,6-difluoro-3-pyridyl)-2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methyl-aniline;4,5-difluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-5-methyl-aniline;5-chloro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-[(4-fluorophenoxy)methyl]-6-(4-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-[6-(trifluoromethyl)-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(6-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(2-fluoro-3-pyridyl)imidazo[1,2-a]pyrimidine;6-(5,6-difluoro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-2-methoxy-aniline;2-[(4-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-2-pyridyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;6-(5-chloro-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(5-methoxy-3-pyridyl)imidazo[1,2-a]pyrimidine;5-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-ol;6-(6-fluoro-5-methyl-3-pyridyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(6-methyl-3-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-(5-fluoro-2-pyridyl)imidazo[1,2-a]pyrimidine;2-[(3-fluorophenoxy)methyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;4-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;[5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;[5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;6-(4-fluoro-2-methylsulfanyl-phenyl)-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine;2-[(4-fluorophenoxy)methyl]-6-(2-methoxy-4-pyridyl)imidazo[1,2-a]pyrimidine;2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]-4-methyl-aniline;5-fluoro-2-[2-[(3-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;6-(4-fluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methylphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(7-fluoro-2H-benzo[1,3]dioxol-4-yl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-2-methoxyphenyl)-2-(pyridin-2-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methoxy-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-[4-fluoro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2-ethylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methyl-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2-fluoro-4-methyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methoxy-phenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(4-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(3-fluoro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(4-fluoro-2-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-(o-tolyl)imidazo[1,2-a]pyrimidine;6-(4-chloro-2-methyl-phenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-dimethylphenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(5-fluoro-2-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-(2-pyridyloxymethyl)-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;2-[(5-fluoro-2-pyridyl)oxymethyl]-6-[6-(trifluoromethyl)-3-pyridyl]imidazo[1,2-a]pyrimidine;6-(5-fluoro-2-pyridyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;2-fluoro-5-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;2-fluoro-5-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]aniline;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;3-methoxy-4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;4-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]-3-methoxy-benzonitrile;6-(4-fluoro-2-methylsulfanyl-phenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;[5-fluoro-2-[2-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]benzonitrile;6-[4-fluoro-2-(methoxymethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;[2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-5-(trifluoromethyl)phenyl]methanol;6-(2-isopropylphenyl)-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;4-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]-3-(trifluoromethyl)benzaldehyde;6-[4-chloro-2-(trifluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(pyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(5-fluoro-pyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(5-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(6-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(5-chloropyridin-3-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,4-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-methoxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2,3-difluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-fluorophenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-methylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(2-hydroxyphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluoro-2-hydroxymethylphenyl)-2-(2-fluoropyridin-4-yloxymethyl)imidazo[1,2-a]pyrimidine;6-(4-fluorophenyl)-2-[(5-fluoro-3-pyridyl)oxymethyl)imidazo[1,2-a]pyrimidine;2-[(2-chloro-4-pyridyl)oxymethyl]-6-(4-fluorophenyl)imidazo[1,2-a]pyrimidine;2-[(5-fluoro-3-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;2-[(2-fluoro-4-pyridyl)oxymethyl]-6-[4-fluoro-2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine;5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;5-fluoro-2-[2-[(2-fluoro-4-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]aniline;[5-fluoro-2-[2-[(5-fluoro-3-pyridyl)oxymethyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methanol;2-(2,4-difluorophenyl)-6-(phenoxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((pyridin-2-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluorophenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2-methylphenyl)-6-((pyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2,4-difluorophenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-(2-methylphenyl)-6-((2-fluoropyridin-4-yloxy)methyl)imidazo[1,2-b][1,2,4]triazine;2-[4-fluoro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(3-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-[4-chloro-2-(trifluoromethyl)phenyl]-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-chloro-2-methyl-phenyl)-6-(2-pyridyloxymethyl)imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-[(6-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine;2-(4-fluoro-2-methyl-phenyl)-6-[(5-fluoro-2-pyridyl)oxymethyl]imidazo[1,2-b][1,2,4]triazine;[5-fluoro-2-[2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(phenoxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylcarbamate;[5-fluoro-2-[2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl]methylacetate;6-[2-(chloromethyl)-4-fluoro-phenyl]-2-[(4-fluorophenoxy)methyl)imidazo[1,2-a]pyrimidine;6-[4-fluoro-2-(fluoromethyl)phenyl]-2-(2-pyridyloxymethyl)imidazo[1,2-a]pyrimidine;and6-[4-fluoro-2-(fluoromethyl)phenyl]-2-[(4-fluorophenoxy)methyl]imidazo[1,2-a]pyrimidine.